Benzoylpyrazole compounds and herbicides containing them

ABSTRACT

A benzoylpyrazole compound represented by the formula (I) or its salt, useful as herbicides and intermediates thereof.

TECHNICAL FIELD

The present invention relates to novel benzoylpyrazole compounds useful as an active ingredient of herbicides.

BACKGROUND ART

WO96/26206, JP-A-50-126830, JP-A-2-288866 and JP-A-2-173 disclose benzoylpyrazole compounds. However, they differ from benzoylpyrazole compounds represented by the following formula (I) in the chemical structure.

DISCLOSURE OF THE INVENTION Object to be Accomplished by the Invention

Heretofore, herbicides which have excellent herbicidal activity against weeds and which are safe for crop plants, have been desired for labor saving in the operation of controlling weeds and for improvement of productivity of agricultural and horticultural plants. However, search for novel compounds suitable for such an object depends on trial and error.

Means to Accomplish the Object

The present inventors have conducted extensive studies on benzoylpyrazole compounds in order to find more excellent herbicides which accomplish the above object and as a result, accomplished the present invention.

Namely, the present invention relates to a benzoylpyrazole compound represented by the formula (I) or its salt:

wherein R¹ is alkyl or cycloalkyl, R² is a hydrogen atom or alkyl, R³ is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl which may be substituted by R⁸, R⁴ is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R⁵ is a hydrogen atom; alkyl; alkenyl; alkynyl; halogen; cyano; cyanoalkyl; cyanoalkenyl; haloalkyl; alkoxyalkyl; haloalkoxyalkyl; amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio) carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷; thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy; haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy; alkoxyhaloalkoxy; haloalkoxyhaloalkoxy; alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio; haloalkoxyalkylthio; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio; alkylthioalkylthio; haloalkylthioalkylthio; alkylthiohaloalkylthio; haloalkylthiohaloalkylthio; alkylthioalkoxy; alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl; alkoxycarbonylalkoxy; heterocyclylalkyl; heterocyclyloxy; heterocyclylalkoxy; heterocyclylalkoxyalkyl; heterocyclyloxyalkyl; cycloalkyloxy; —OC(O)SR⁷, —OC(O)OR⁷; —C(O)OR⁷; —C(O)SR⁷; —C(S)OR⁷; —C(S)SR⁷; aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷; or 4,5-dihydroisoxazol-3-yl which may be substituted by R⁹, R⁶ is haloalkyl; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R⁷ is alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl which may be substituted by R¹⁰, and each of R⁸, R⁹ and R¹⁰ which are independent of one another, is halogen; alkyl; or alkoxy, a process for producing it, a herbicide containing it as an active ingredient, and a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of it to the undesired plants or to a place where they grow.

The compounds represented by the formula (I) have excellent herbicidal effects.

BEST MODE FOR CARRYING OUT THE INVENTION

The alkyl or alkyl moiety in each of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹¹ may be linear or branched, and specific examples thereof include C₁₋₉ alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, n-hexyl, iso-hexyl, n-heptyl, n-octyl and n-nonyl.

Examples of the cycloalkyl or cycloalkyl moiety in each of R¹, R³ and R⁵ include C₃₋₆ cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The alkenyl or alkenyl moiety in each of R³, R⁵ and R⁷ may be linear or branched, and specific examples thereof include C₂₋₉ alkenyl such as vinyl, 1-propenyl, 2-propenyl, iso-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 2-pentenyl, 4-pentenyl, 2-hexenyl, 4-hexenyl, 2-heptenyl, 4-heptenyl, 2-octenyl, 6-octenyl and 2-nonenyl.

The alkynyl or alkynyl moiety in each of R⁵ and R⁷ may be linear or branched, and specific examples thereof include C₂₋₉ alkynyl such as ethynyl, propargyl, 1-propynyl, 1-pentynyl, 3-pentynyl, 1-heptynyl and 1-nonynyl.

Examples of halogen or halogen as the substituent in each of R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ include atoms of fluorine, chlorine, bromine and iodine.

The number of halogens as substituents in each of R³, R⁴, R⁵, R⁶ and R⁷ may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution of such halogens may be any positions.

The number of alkoxy or alkoxy moieties as substituents in each of R³, R⁵ and R⁷ may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution may be any positions.

Examples of the aryl or aryl moiety as the substituent in each of R³ and R⁷ include phenyl and naphthyl. The number of aryl or aryl moieties as substituents may be 1 or more, and if more, they may be is the same or different. Further, the positions for substitution may be any positions.

The number of R⁸ as substituents which substitute the arylalkyl in R³ may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution of such substituents may be any positions.

The number of R¹⁰ as substituents which substitute the arylalkyl in R⁷ may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution of such substituents may be any positions.

The number of R⁹ as substituents which substitute the 4,5-dihydroisoxazol-3-yl in R⁵ may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution of such substituents may be any positions.

The alkoxyalkoxy in R⁵ is meant for an alkoxy group having the same or different alkoxy moiety bonded thereto. The position for substitution of the alkoxy moiety which substitutes the alkoxy group may be any position. The same applies to haloalkoxyalkoxy, alkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthioalkylthio, alkylsulfonylalkyl, alkoxycarbonylalkyl, etc.

The heterocyclyl moiety in R⁵ may, for example, be a saturated or unsaturated 5-membered or 6-membered ring containing 1 to 4 one or more types of hetero atoms optionally selected from O, S and N, and specific examples thereof include oxolanyl, 1,3-dioxolanyl, tetrahydrofuranyl and tetrahydro-2H-pyranyl. Further, the number of heterocyclyl moieties as substituents may be 1 or more, and if more, they may be the same or different. The positions for substitution of the heterocyclyl moieties may be any positions.

The salt of the benzoylpyrazole compound represented by the above formula (I) includes all kinds of salts so long as they are agriculturally acceptable. Examples thereof include alkali metal salts such as a sodium salt and a potassium salt; alkaline earth metal salts such as a magnesium salt and a calcium salt; amine salts such as a dimethylamine salt and a triethylamine salt; inorganic acid salts such as a hydrochloride, a perchlorate, a sulfate and a nitrate; and organic acid salts such as an acetate and a methanesulfonate.

The benzoylpyrazole compound represented by the above formula (I) or its salt (hereinafter referred to simply as the compound of the present invention) can be produced by the following reactions [A] to [AG] and in accordance with a usual method for producing a salt.

The compound of the present invention represented by the above formula (I) can be produced in accordance with the following reaction [A].

wherein R¹, R², R³, R⁴, R⁵ and R⁶ are as defined above, and Z is a leaving group such as halogen.

Namely, the compound of the present invention represented by the above formula (I) can be produced by reacting a compound represented by the formula (II) with a compound represented by the formula (III).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried-out in the presence of a base, as the case requires. The base may be either inorganic base or organic base. Examples of the inorganic base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkaline earth metal hydroxides such as calcium hydroxide; and alkaline earth metal carbonates such as calcium carbonate. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. As the base, one or more types may suitably be selected and mixed.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The above reaction may also be carried out in the two-phase system in water and a solvent insoluble in water among the above solvents in the presence of a phase transfer catalyst such as a quaternary ammonium salt.

As mentioned above; compounds represented by the above formula (II) are useful as an intermediate for preparation of the compounds represented by the formula (I). Further, some of the compounds represented by the formula (II) are novel, which are exemplified below.

Benzoylpyrazole compounds represented by the formula (II-x) or their salts:

wherein R¹ is alkyl or cycloalkyl, R² is a hydrogen atom or alkyl, R⁴ is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R^(5-x) is alkyl substituted by at least 2 alkoxy; alkyl substituted by at least 2 haloalkoxy; amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷; thiocyanatoalkyl; alkoxy substituted by at least 2 alkoxy, alkoxy substituted by at least 2 haloalkoxy; alkoxyhaloalkoxy; haloalkoxyhaloalkoxy; alkoxyalkyl substituted by at least 2 alkoxy; alkylthio substituted by at least 2 alkoxy; alkylthio substituted by at least 2 haloalkoxy; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio; alkylthioalkylthio; haloalkylthioalkylthio; alkylthiohaloalkylthio; haloalkylthiohaloalkylthio; alkylthioalkoxy; alkyl substituted by at least 2 alkylsulfonyl; alkyl substituted by at least 2 alkoxycarbonyl; alkoxy substituted by at least 2 alkoxycarbonyl; alkyl substituted by at least 2 heterocyclyl; alkoxy substituted by at least 2 heterocyclyl; alkyl substituted by at least 2 heterocyclylalkoxy; —OC(O)SR⁷; or aminoalkyl which may be substituted by at least one substituent selected from cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷, R⁶ is haloalkyl; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R⁷ is alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl, which may be substituted by R¹⁰, and R¹⁰ is halogen; alkyl; or alkoxy.

In addition, among the compounds of the present invention represented by the above formula (I), a compound wherein R³ is R^(3-a) can be produced in accordance with the following reaction [B-1].

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above, R^(3-a) is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl which may be substituted by R⁸.

Namely, the compound of the present invention represented by the above formula (I-a) can be produced by reacting a compound represented by the formula (IV-a) or the formula (V-a) with a compound represented by the formula (VI-a), or by reacting a mixture of a compound represented by the formula (IV-a) and a compound represented by the formula (V-a) with a compound represented by the formula (VI-a).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may be either inorganic base or organic base. Examples of the inorganic base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkaline earth metal hydroxides such as calcium hydroxide; and alkaline earth metal carbonates such as calcium carbonate. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. As the base, one or more types may suitably be selected and mixed.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds of the present invention represented by the above formula (I), a compound wherein R³ is R^(3-b) can be produced in accordance with the following reaction [B-2].

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above, and R^(3-b) is alkenyl.

Namely, the compound of the present invention represented by the above formula (I-b) can be produced by reacting a compound represented by the formula (IV-b) or the formula (V-b) with a compound represented by the formula (VI-b), or by reacting a mixture of a compound represented by the formula (IV-b) and a compound represented by the formula (V-b) with a compound represented by the formula (VI-b).

The above reaction can be carried out in the presence of a solvent, as the case requires. Examples of the solvent include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may be either inorganic base or organic base. Examples of the inorganic base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkaline earth metal hydroxides such as calcium hydroxide; and alkaline earth metal carbonates such as calcium carbonate. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. As the base, one or more types may suitably be selected and mixed.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The above compound represented by the formula (IV-a) or the formula (V-a) or a mixture thereof can be produced in accordance with the following reaction [C-1].

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above.

Namely, the compound represented by the formula (IV-a) or the formula (V-a) or a mixture thereof can be produced by reacting a compound represented by the formula (II) with phosgene (COCl₂).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may be either inorganic base or organic base. Examples of the inorganic base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkaline earth metal hydroxides such as calcium hydroxide; and alkaline earth metal carbonates such as calcium carbonate. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. As the base, one or more types may suitably be selected and mixed.

The above reaction can be carried out at a reaction temperature of usually from −10° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The above compound represented by the formula (IV-b) or the formula (V-b) or a mixture thereof can be produced in accordance with the following reaction [C-2].

wherein R¹, R²R⁴, R⁵ and R⁶ are as defined above.

Namely, the compound represented by the formula (IV-b) or the formula (V-b) or a mixture thereof can be produced by reacting a compound represented by the formula (II) with thiocarbonyl chloride (CSCl₂).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may be either inorganic base or organic base. Examples of the inorganic base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkaline earth metal hydroxides such as calcium hydroxide; and alkaline earth metal carbonates such as calcium carbonate Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. As the base, one or more types may suitably be selected and mixed.

The above reaction can be carried out at a reaction temperature of usually from −10° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (II), some compounds are known compounds, such as a compound wherein R⁴ is alkyl, R⁵ is alkoxyalkyl, alkoxycarbonyl, alkoxyalkoxycarbonyl or haloalkoxycarbonyl, and R⁶ is alkylsulfonyl, as disclosed in European Patent Publication No. 0282944, at pages 36 to 41, a compound wherein R⁴ is halogen, R⁵ is alkoxyalkoxy or heterocyclylalkoxy, and R⁶ is alkylsulfonyl, as disclosed in European Patent Publication No. 0352543, at pages 16 to 20, a compound wherein R⁴ is halogen, R⁵ is alkoxyalkoxyalkyl or alkoxy, and R⁶ is alkylsulfonyl, as disclosed in European Patent Publication No. 0344775, at pages 25 to 27, and a compound wherein R⁴ is halogen, R⁵ is 4,5-dihydroisoxazol-3-yl, and R⁶ is halogen or alkylsulfonyl, as disclosed in WO98/31681, at pages 121 to 127, and they can be produced in accordance with a method disclosed in each publication or a method similar thereto.

The compound represented by the above formula (II) can be produced in accordance with the following reaction [D].

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above.

Namely, the compound represented by the formula (II) can be produced by subjecting a compound represented by the formula (VII) to rearrangement reaction.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may be either organic base or inorganic base. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal cyanides such as sodium cyanide and potassium cyanide. As the base, one or more types may suitably be selected and mixed in an amount of from 0.01 to 100 equivalent amounts based on the compound of the formula (VII).

Further, for the above reaction, a catalyst may be added as the case requires. As the catalyst, acetone cyanohydrin can be used in an amount of from 0.01 to 10 equivalent amounts based on the compound of the formula (VII).

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (VII) can be produced in accordance with the following reaction [E].

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above.

Namely, the compound represented by the formula (VII) can be produced by reacting a compound represented by the formula (VIII) or its salt, such as a hydrochloride, a sulfate or a nitrate, with a compound represented by the formula (IX).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above-reaction can be carried out in the presence of a base, as the case requires. The base may be either inorganic base or organic base. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal carbonates such as calcium carbonate and magnesium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; and alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. As the base, one or more types may suitably be selected and mixed in an amount of from 1 to 100 equivalent amounts based on the compound of the formula (IX).

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (IX) can be produced in accordance with the following reaction [F].

wherein R⁴, R⁵ and R⁶ are as defined above.

Namely, the compound represented by the formula (IX) can be produced by reacting a compound represented by the formula (X) with a halogenating agent. This reaction is a method disclosed in literature (Organic Syntheses, Collective Volume 4, page 715, Collective Volume 9, page 516, etc.).

In the above reaction, a halogenating agent such as thionyl chloride or oxalyl chloride is reacted in an amount of from 1 to 100 equivalent amounts based on the compound represented by the formula (X).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

For the above reaction, a catalyst can be used, as the case requires. The catalyst may, for example, be DMF.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

In addition to the above processes, the compound represented by the formula (VII) can be produced in is accordance with the following reaction [G].

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above.

Namely, the compound represented by the formula (VII) can be produced by reacting a compound represented by the formula (VIII) or its salt, such as a hydrochloride, a sulfate or a nitrate, with a compound represented by the formula (X) by means of a dehydrating agent.

The dehydrating agent to be used for the above reaction may, for example, be DCC (dicyclohexylcarbodiimide) or 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. Examples of the base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. As the base, one or more types may suitably be selected and mixed in an amount of from 1 to 100 equivalent amounts based on the compound represented by the formula (X).

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the formula (X), compounds wherein R⁴ is alkyl, R⁵ is haloalkoxy, and R⁶ is alkylthio or alkylsulfonyl, are known compounds disclosed in WO96/14285, pages 31 and 32, etc. They can be produced in accordance with a method disclosed in the publication, etc. or a method similar thereto.

The compound represented by the above formula (X) can be produced in accordance with the following reaction [H].

wherein R⁴, R⁵ and R⁶ are as defined above, and L is a protective group such as alkyl.

The compound represented by the formula (X) can be produced by subjecting a compound represented by the formula (XI) to hydrolysis.

The above reaction can be carried out in the presence of a solvent, as the case requires. Examples include aromatic hydrocarbons such as benzene, toluene and xylene; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; ethers such as diethyl ether, dioxane and tetrahydrofuran; alcohols such as methanol and ethanol; and water. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base or an acid, as the case requires. The base may be either inorganic base or organic base. Examples of the inorganic base include alkali metal hydroxides such as lithium hydroxide and sodium hydroxide; alkali metal carbonates such as potassium carbonate and sodium carbonate; and alkaline earth metal carbonates such as calcium carbonate and barium carbonate. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine. Examples of the acid include hydrochloric acid, sulfuric acid and perchloric acid. As the base or acid, one or more types may suitably be selected and mixed in an amount of from 1 to 100 equivalent amounts based on the compound represented by the formula (XI).

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (XI), a compound represented by the formula (XI-a-1) wherein R⁵ is R^(5-a-1) can be produced in accordance with the following reaction [I].

wherein R⁴, R⁶ and L are as defined above, R^(5-a-1) alkoxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, heterocyclyloxy, heterocyclylalkoxy, cycloalkyloxy, —OC(O)SR⁷, —OC(O)OR⁷, alkylthioalkoxy, alkoxycarbonylalkoxy, alkenyloxy or alkynyloxy and R^(α) is alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, heterocyclyl, heterocyclylalkyl, cycloalkyl, —C(O)SR⁷, —C(O)OR⁷, alkylthioalkyl, alkoxycarbonylalkyl, alkenyl or alkynyl.

Namely, the compound represented by the formula (XI-a-1) can be produced by reacting a compound represented by the formula, (XII) with a compound represented by the formula (XIII) by means of a dehydrating agent.

The dehydrating agent to be used in the above reaction may, for example, be DCC (dicyclohexylcarbodiimide), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride or diethylazodicarboxylate.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. Examples of the base include tertiary amines such as triethylamine and diisopropylethylamine; pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. As the base, one or more types may suitably be selected and mixed in an amount of from 1 to 100 equivalent amounts based on the compound represented by the formula (XII).

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (XII), compounds wherein R⁴ is alkyl, and R⁶ is alkylthio or alkylsulfonyl, are known compounds disclosed in WO97/35851, at pages 54 to 55, etc. They can be produced in accordance with a method disclosed in the publication, etc. or a method similar thereto.

In addition to the above processes, the compound represented by the formula (XI-a-1) can also be produced in accordance with the following reaction [J].

wherein R⁴, R^(5-a-1), R⁶, R^(α) and L are as defined above, and X is a leaving group such as halogen or a methanesulfonyloxy group.

Namely, the compound represented by the formula (XI-a-1) can be produced by reacting a compound represented by the formula (XII) with a compound represented by the formula (XIV) in the presence of a base.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The base to be used in the above reaction may be either inorganic base or organic base. Examples of the organic base include triethylamine, diisopropylethylamine, pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal hydrides such as sodium hydride and potassium hydride. As the base, one or more may suitably be selected and mixed in an amount of from 0.5 to 100 equivalent amounts based on the compound of the formula (XII).

The above reaction can be carried out in the presence of a catalyst, as the case requires. The catalyst may, for example, be potassium iodide or tetra-n-butylammonium iodide.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XII) can be produced in accordance with the following reaction [K].

wherein R⁴, R⁶ and L are as defined above.

Namely, the compound represented by the formula (XII) can be produced by reacting a compound represented by the formula (XV) with a Lewis acid such as BBr₃.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, and esters such as methyl acetate, ethyl acetate and propyl acetate. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XV) can be produced in accordance with the following reaction [L].

wherein R⁴, R⁶ and L are as defined above.

Namely, the compound represented by the formula (XV) can be produced by a reaction of introducing a protective group L into a compound represented by the formula (XVI).

The above reaction can be carried out in the presence of a solvent, as the case requires. Examples of the solvent include alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene, toluene and xylene; esters such as methyl acetate, ethyl acetate and propyl acetate; halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; and aprotic polar solvents such as acetonitrile, N,N-dimethylformamide; dimethylsulfoxide, sulfolane and dimethoxyethane. As the solvent, one or more may suitably be selected.

The above reaction can be carried out in the presence of an acid, as the case requires. Examples of the acid to be used for the above reaction include hydrochloric acid and sulfuric acid.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XVI) can be produced in accordance with a known method. For example, among the compounds represented by the formula (XVI), a compound wherein R⁴ is alkyl, and R⁶ is alkylsulfonyl, as disclosed in WO93/13060, at page 4, and a compound wherein R⁴ is halogen, and R⁶ is alkylsulfonyl, as disclosed in JP-A-2-45448, at page 6, are known compounds, and they can be produced in accordance with a method disclosed in each publication or a method similar thereto.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-2) can be produced in accordance with the following reaction [M].

wherein R⁴, R⁶ and L are as defined above, and R^(5-a-2) is alkylthiocarbonyl.

Namely, the compound represented by the formula (XI-a-2) can be produced by reacting a compound represented by the formula (XVIII) with alkylthiol.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include ethers such as diethyl ether, dioxane and tetrahydrofuran; aromatic hydrocarbons such as benzene, toluene and xylene; esters such as methyl acetate, ethyl acetate and propyl acetate; and halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may be either inorganic base or organic base Examples of the organic base include triethylamine, diisopropylethylamine, pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. Examples of, the inorganic base include alkali metal carbonates such as potassium carbonate and sodium carbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal hydrides such as sodium hydride and potassium hydride. As the base, one or more types may suitably be selected and mixed.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XVIII) can be produced in accordance with the following reaction [N].

wherein R⁴, R⁶ and L are as defined above.

Namely, the compound represented by the formula (XVIII) can be produced by reacting a compound represented by the formula (XIX) with a halogenating agent. This reaction can be carried out in the same manner as the above-described reaction [F].

The compound represented by the above formula (XIX) can be produced in accordance with the following reaction [O].

wherein R⁴, R⁶ and L are as defined above.

Namely, the compound represented by the formula (XIX) can be produced by oxidizing a compound represented by the formula (XX).

The oxidizing agent in the above reaction may, for example, be potassium permanganate or chromium trioxide.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate, ethyl acetate and propyl acetate; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XX) can be produced in accordance with the following reaction [P].

wherein R⁴, R⁶ and L are as defined above.

Namely, the compound represented by the formula (XX) can be produced by reacting a compound represented by the formula (XXI) with an oxidizing agent in the presence of a solvent.

The oxidizing agent to be used for the above reaction may, for example, be N-methylmorpholine oxide.

The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction. Examples thereof include aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compounds represented by the above formula (XX) and the formula (XXI) can be produced by known methods. For example, among the compounds represented by the formulae (XX) and (XXI), a compound wherein R⁴ is alkyl, and R⁶ is alkylsulfonyl, as disclosed in JP-A-11-240872, at page 9, and a compound wherein R⁴ is halogen, and R⁶ is alkylsulfonyl, as disclosed in WO98/29392, at page 264, are known compounds, and they can be produced in accordance with a method disclosed in each publication or a method similar thereto.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-3) can be produced in accordance with the following reaction [Q].

wherein R⁴, R⁶ and L are as defined above, and R^(5-a-3) is alkylsulfonylalkyl.

Namely, the compound represented by the formula (XI-a-3) can be produced by reacting a compound represented by the formula (XXII) with an oxidizing agent in the presence of a solvent.

The oxidizing agent to be used for the above reaction may, for example, be hydrogen peroxide, peracetic acid or m-chloroperbenzoic acid.

The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; ketones such as acetone and dimethyl ethyl ketone; ethers such as diethyl ether, dioxane and tetrahydrofuran; and acetic acid. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XXII) can be produced in accordance with the following reaction [R].

wherein R⁴, R⁶ and L are as defined above.

Namely, the compound represented by the above formula (XXII) can be produced by reacting a compound represented by the formula (XXIII) with an alkylthiol in the presence of a solvent.

The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; ketones such as acetone and dimethyl ethyl ketone; ethers such as diethyl ether, dioxane and tetrahydrofuran; acetic acid; water; and N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may be either inorganic base or organic base. Examples of the organic base include triethylamine, diisopropylethylamine, pyridine, 4-(dimethylamino)pyridine and 2,6-lutidine. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkaline earth metal carbonates such as calcium carbonate and magnesium carbonate; alkali metal hydroxides such as sodium hydroxide; and alkali metal hydrides such as sodium hydride and potassium hydride. As the base, one or more types may suitably be selected and mixed.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XXIII) can be produced by a known method. For example, a compound wherein R⁴ is alkyl and R⁶ is alkylsulfonyl, as disclosed in JP-A-11-240872, at page 9, and a compound wherein R⁴ is halogen and R⁶ is alkylsulfonyl, as disclosed in WO98/29392, at page 264, are known compounds, and they can be produced in accordance with a method disclosed in each publication or a method similar thereto.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-4) can be produced in accordance with the following reaction [S].

wherein R⁴, R⁶ and L are as defined above, and R^(5-a-4) is cyano.

Namely, the compound represented by the formula (XI-a-4) can be produced by reacting a compound represented by the formula (XXIV) with an acid anhydride such as acetic anhydride or sulfonyl chloride such as methanesulfonyl chloride.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; ketones such as acetone and dimethyl ethyl ketone; ethers such as diethyl ether, dioxane and tetrahydrofuran; and pyridine. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. Examples of the base include triethylamine, N,N-dimethylaminopyridine and diisopropylaminopyridine. As the base, one or more types may suitably be selected and mixed.

The above reaction can be carried out at a reaction temperature of usually from 0 to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XXIV) can be produced in accordance with the following reaction [T].

wherein R⁴, R⁶ and L are as defined above.

Namely, the compound represented by the formula (XXIV) can be produced by reacting a compound represented by the formula (XX) with hydroxyamine or hydroxyamine hydrochloride in the presence of a solvent.

The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction. Examples thereof include alcohols such as methanol and ethanol; halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; ketones such as acetone and dimethyl ethyl ketone; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of an acid or a base, as the case requires. Examples of the acid include p-toluenesulfonic acid. Examples of the base include sodium acetate.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-5) can be produced in accordance with the following reaction [U].

wherein R⁴, R⁶ and L are as defined above, and R^(5-a-5) is cyanoalkyl.

Namely, the compound represented by the formula (XI-a-5) can be produced by reacting a compound represented by the formula (XXV) with an acid anhydride such as acetic anhydride or sulfonyl chloride such as methanesulfonyl chloride. This reaction can be carried out in the same manner as the above-described reaction [S].

The compound represented by the above formula (XXV) can be produced in accordance with the following reaction [V].

wherein R⁴, R⁶ and L are as defined above

Namely, the compound represented by the formula (XXV) can be produced by reacting a compound represented by the formula (XXVI) with hydroxyamine or hydroxyamine hydrochloride in the presence of a solvent. This reaction can be carried out in the same manner as the above-described reaction [T].

The compound represented by the above formula (XXVI) is can be produced in accordance with the following reaction [W].

wherein R⁴, R⁶ and L are as defined above, and A is alkyl.

Namely, the compound represented by the formula (XXVI) can be produced by reacting a compound of the formula (XXVII) with an acid such as hydrochloric acid.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction. Examples thereof include water; alcohols such a methanol and ethanol; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XXVII) can be produced in accordance with the following reaction [X].

wherein R⁴, R⁶, L and A are as defined above.

Namely, the compound represented by the formula (XXVII) can be produced by reacting a compound represented by the formula (XXVIII) with an alcohol in the presence of an acid.

The alcohol to be used for the above reaction may, for example, be methanol or ethanol. Further, the acid may, for example, be hydrochloric acid or toluenesulfonic acid.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XXVIII) can be produced in accordance with the following reaction [Y].

wherein R⁴, R⁶ and L are as defined above, T is halogen, Ph is phenyl, and Me is methyl.

Namely, the compound represented by the formula (XXVIII) can be produced by subjecting a compound represented by the formula (XX) to Wittig reaction in the presence of a solvent.

The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction. Examples thereof include ethers such as diethyl ether, dioxane and tetrahydrofuran; aromatic hydrocarbons such as benzene, toluene and xylene; and aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane.

The above reaction can be carried out in the presence of a base, as the case requires. Examples of the base include sodium hydride (NaH); alkali lithium agents such as n-butyllithium; and metal amides such as sodium amide (NaNH₂).

The above reaction can be carried out at a reaction temperature of usually from −80° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-6) can be produced in accordance with the following reaction [Z].

wherein R⁴, R⁶ and L are as defined above, and R^(5-a-5) is alkoxyalkoxyalkyl.

Namely, the compound represented by the formula (XI-a-6) can be produced by reacting a compound represented by the formula (XXIII) with an alkoxyalcohol.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction, and examples thereof include alcohols such as methanol and ethanol; esters such as methyl acetate, ethyl acetate and propyl acetate; ethers such as diethyl ether, dioxane and tetrahydrofuran; and aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane. As the solvent, one or more may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XXIII) can be produced by a known method. For example, a compound wherein R⁴ is alkyl and R⁶ is alkylsulfonyl, as disclosed in JP-A-11-240872, at page 9, and a compound wherein R⁴ is halogen and R⁶ is alkylsulfonyl, as disclosed in WO98/29392, at page 264, are known compounds, and they can be produced in accordance with a method disclosed in each publication or a method similar thereto.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-7) can be prepared in accordance with the following reaction [AA].

wherein R⁴, R⁶ and L are as defined above, and R^(5-a-7) is alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkoxyhaloalkylthio, haloalkoxyhaloalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthiohaloalkylthio or haloalkylthiohaloalkylthio.

Namely, the compound represented by the formula (XI-a-7) can be produced by reacting a thiol corresponding to R^(5-a-7) with a compound represented by the formula (XXIX).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction, and examples thereof include alcohols such as methanol and ethanol; ethers such as diethyl ether, dioxane and tetrahydrofuran; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and water. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkaline earth metal hydroxides such as calcium hydroxide.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 250° C. for a reaction time of usually from 1 minute to 48 hours.

The compound represented by the above formula (XXIX) can be produced by a known method. For example, a compound wherein R⁴ is halogen and R⁶ is alkylsulfonyl, as disclosed in European Patent Publication No. 0195247, at page 8, and a compound wherein R⁴ is alkyl and R⁶ is alkylsulfonyl, as disclosed in Pest Management Science (2002), 58(12), 1175 to 1186, are known compounds, and they can be produced in accordance with a method disclosed in the publication or a method similar thereto.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-8) can be prepared in accordance with following reaction [AB].

wherein R⁴, R⁶ and L are as defined above, and R^(5-a-8) is a heterocyclylalkyl containing two oxygen atoms.

Namely, the compound represented by the formula (XI-a-8) can be produced by reacting an alkylene glycol with a compound represented by the formula (XXVI) in the presence of a solvent and an acid catalyst.

The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The acid catalyst to be used for the above reaction may, for example, be p-toluenesulfonic acid or pyridium p-toluenesulfonate.

In the above reaction, it is preferred to remove moisture generated by the reaction by azeotropy with the solvent or by using a drying agent.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (II), a compound wherein R⁵ is R^(5-a-9) can be prepared in accordance with the following reaction [AC].

wherein R¹, R², R⁴ and R⁶ are as defined above, and R^(5-a-9) is thiocyanatoalkyl.

Namely, the compound represented by the formula (II-a-9) can be produced by reacting NaSCN with a compound represented by the formula (II-a-10).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; ethers such as diethyl ether, dioxane and tetrahydrofuran; and alcohols such as methanol, ethanol and propanol. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-10) can be prepared in accordance with the following reaction [AD].

wherein R⁴, R^(5-a-5), R⁶ and L are as defined above, and R^(5-a-10) is amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷.

Namely, the compound represented by the formula (XI-a-10) can be produced by reacting P₂S₅ with a compound represented by the formula (XI-a-5) in the presence of a solvent.

The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction, and examples thereof include alcohols such as methanol, ethanol and propanol; halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene; esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 250° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-11) can be prepared in accordance with the following reaction [AE].

wherein R⁴, R⁶ and L are as defined above, and R^(5-a-11) is aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷.

Namely, the compound represented by the formula (XI-a-11) can be produced by reacting ammonia or an amine which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷, with a compound represented by the formula (XXIII).

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent to be used for the above reaction may be any solvent so long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene, esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may is be either inorganic base or organic base. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkaline earth metal carbonates such as calcium carbonate and magnesium carbonate; sodium hydride (NaH); alkali lithium reagents such as n-butyllithium; and metal amides such as sodium amide (NaNH₂). Examples of the organic base include amines such as triethylamine, N,N-dimethylaminopyridine, diisopropylaminopyridine and DBU (diazabicycloundecene).

The above reaction can be carried out in the presence of a catalyst, as the case requires. The catalyst may, for example, be TBAI (tert-butylammonium iodide).

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-12) can be prepared in accordance with the following reaction [AF-1].

wherein R⁴, R⁶, R^(5-a-11) and L are as defined above, and R^(5-a-12) is one having the amino moiety of R^(5-a-11) substituted by alkyl or cyanoalkyl.

Namely, the compound represented by the formula (XI-a-12) can be produced by reacting a compound represented by the formula (XI-a-11) with an alkyl halide or a cyanoalkyl halide.

The above reaction can be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction, and examples thereof include alcohols such as methanol, ethanol and propanol; halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane and trichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene; esters such as methyl acetate, ethyl acetate and propyl acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, sulfolane and dimethoxyethane; and ethers such as diethyl ether, dioxane and tetrahydrofuran. As the solvent, one or more types may suitably be selected.

The above reaction can be carried out in the presence of a base, as the case requires. The base may be either inorganic base or organic base. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogencarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; and alkaline earth metal carbonates such as calcium carbonate and magnesium carbonate. Examples of the organic base include amines such as triethylamine, N,N-dimethylaminopyridine, diisopropylaminopyridine and DBU (diazabicycloundecene).

The above reaction can be carried out at a reaction temperature of usually from 0° C. to 150° C. for a reaction time of usually from 1 minute to 48 hours.

Among the compounds represented by the above formula (I), a compound wherein R⁵ is R^(5-a-13) can be prepared in accordance with the following reaction [AF-2].

wherein R¹, R², R⁴, R⁶R^(5-a-11) and Z are as defined above, and R^(5-a-13) is one having the amino moiety of R^(5-a-11) substituted by (alkylthio)carbonyl.

Namely, the compound represented by the formula (I-a-13) can be produced by reacting a compound represented by the formula (II-a-11) with a compound represented by the formula (III-a). This reaction can be carried out in the same manner as the above-described reaction [A].

Among the compounds represented by the above formula (XI), a compound wherein R⁵ is R^(5-a-14) can be prepared in accordance with the following reaction [AG].

wherein R⁴, R⁶, L, T and Ph are as defined above, and R^(5-a-14) is cyanoalkenyl.

Namely, the compound represented by the formula (XI-a-15) can be produced by subjecting a compound represented by the formula (XX) to Wittig reaction in the presence of a solvent. This reaction can be carried, out in the same manner as the above-described reaction [Y].

The compounds of the present invention have excellent herbicidal effects when used as an active ingredient of herbicides. The application range extends to agricultural fields such as paddy fields, crop plant fields, orchards and mulberry fields and non-agricultural fields such as forest land, farm roads, play grounds and factory sites. The application method may suitably be selected from soil application, foliar application, water application, etc.

The compounds of the present invention are capable of controlling a wide range of undesired plants such as grasses (or gramineae) such as barnyardgrass (Echinochloa crus-galli L.), early watergrass (Echinochloa oryzicola vasing), crabgrass (Digitaria sanguinalis L.), greenfoxtail (Setaria viridis L.), giant foxtail (Setaria faberi Herrm.), goosegrass (Eleusine indica L.), wild oat (Avena fatua L.), johnsongrass (Sorghum halepense L.), quackgrass (Agropyron repens L.), alexandergrass (Brachiaria plantaginea), paragrass (Panicum purpurascens), sprangletop (Leptochloa chinensis), red sprangletop (Leptochloa panicea), annual bluegrass (Poa annua L.), black grass (Alopecurus myosuroides Huds.) and cholorado bluestem (Agropyron tsukushiense (Honda) Ohwi), sedges (or Cyperaceae) such as rice flatsedge (Cyperus iria L.), purple nutsedge (Cyperus rotundus L.), yellow nutsedge (Cyperus esculentus L.), japanese bulrush (Scirpus juncoides), flatsedge (Cyperus serotinus), small-flower umbrellaplant (Cyperus difformis), slender spikerush (Eleocharis acicularis) and water chestnut (Eleocharis kuroguwai), alismataceae such as japanese ribbon waparo (Sagittaria pygmaea), arrow-head (Sagittaria trifolia) and narrowleaf waterplantain (Alisma canaliculatum), pontederiaceae such as monochoria (Monochoria Vaginalis) and monochoria species (Monochoria korsakowii), scrophulariaceae such as false pimpernel (Lindernia pyxidaria) and abunome (Dopatrium junceum), lythraceae such as toothcup (Rotala india) and red stem (Ammannia multiflora), and other broad leaves such as velvetleaf (Abutilon theophrasti MEDIC.), tall morningglory (Ipombea purpurea L.), common lambsquarters (Chenopodium album L.), prickly sida (Sida spinosa L.), common purslane (Portulaca oleracea L.), slender amaranth (Amaranthus viridis L.), redroot pigweed (Amaranthus retroflexus L.), sicklepod (Cassia obtusifolia L.), black nightshade (Solanum nigrum L.), pale smartweed (Polygonum lapathifolium L.), common chickweed (Stellaria media L.), long stem waterwort (Elatine triandra SCHK.), common cocklebur (Xanthium strumarium L.), flexuous bittercress (Cardamine flexuosa WITH.), henbit (Lamium amplexicaule L.), common ragweed (Ambrosia elatior L.), catchweed (Galium spurium L.), field bindweed (Calystegia arvensis L.), jimsonweed (Datura stramonium), thistle (Breea setosa (BIEB.)KITAM.) and threeseeded copperleaf (Acalypha australis L.). Therefore, they can be effectively used for selectively controlling noxious weeds or nonselectively controlling noxious weeds in cultivation of useful crops such as corn (Zea mays L.), soybean (Glycine max Merr.), cotton (Gossypium spp.), wheat (Triticum spp.), rice (Oryza sativa L.), barley (Hordeum vulgare L.), oat (Avena sativa L.), sorgo (Sorghum bicolor Moench), rape (Brassica napus L.), sunflower (Helianthus annuus L.), sugar beet (Beta vulgaris L.), sugar cane (Saccharum officinarum L.), japanese lawngrass (Zoysia japonica stend), peanut (Arachis hypogaea L.), flax (Linum usitatissimum L.), tobacco (Nicotiana tabacum L.), and coffee (Coffea spp.). Particularly, the compounds of the present invention are effectively used for selectively controlling noxious weeds in cultivation of corn, soybean, cotton, wheat, rice, rape, sunflower, sugar beet, sugar cane, japanese lawngrass, peanut, flax, tobacco, coffee, and the like, and among these, especially corn, soybean, wheat, rice and the like.

The compound of the present invention may be mixed with various agricultural additives and applied in the form of various formulations such as dusts, granules, water dispersible granules, wettable powders, tablets, pills, capsules (including a formulation packaged by a water soluble film), water-based suspensions, oil-based suspensions, microemulsions, suspoemulsions, water soluble powders, emulsifiable concentrates, soluble concentrates or pastes. It may be formed into any formulation which is commonly used in this field, so long as the object of the present invention is thereby met.

The additives to be used for the formulation include, for example, a solid carrier such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite or starch; a solvent such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N,N-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone or an alcohol; an anionic surfactant such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, a salt of polyoxyethylene aryl ether phosphoric acid ester, a naphthalene sulfonate condensed with formaldehyde or an alkylnaphthalene sulfonate condensed with formaldehyde; a nonionic surfactant such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, polyethylene glycol, a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil or a polyoxypropylene fatty acid ester; and a vegetable oil or mineral oil such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil or liquid paraffins. These additives may suitably be selected for use alone or in combination as a mixture of two or more of them, so long as the object of the present invention is met. Further, additives other than the above-mentioned may be suitably selected for use among those known in this field. For example, various additives commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a safener, an anti-mold agent, a bubble agent, a disintegrator and a binder, may be used. The mix ratio by weight of the compound of the present invention to such various additives may be from 0.1:99.9 to 95:5, preferably from 0.2:99.8 to 85:15.

The dose of the herbicide containing the compound of the present invention can not generally be defined, as it varies depending upon the weather conditions, the soil conditions, the type of the formulation, the type of the weeds to be controlled, the application season, etc. However, it is usually applied in an amount of the compound of the present invention of from 0.5 to 5,000 g, preferably from 1 to 1,000 g, more preferably from 10 to 500 g, per hectare. The present invention includes such a method for controlling undesired weeds, by such applications of the herbicide.

Further, the herbicide containing compound of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity-reducing agents, whereby synergistic effects or activities may sometimes be obtained. Such other agricultural chemicals include, for example, a herbicide, a fungicide, an antibiotic, a plant hormone and an insecticide. Especially, with a mixed herbicidal composition having a compound of the present invention mixed with or used in combination with one, or more active compounds of other herbicides, the range of weeds to be controlled, the time of application of the composition, the herbicidal activities, etc. may be improved to preferred directions. The compound of the present invention and the active compounds of other herbicides may separately be formulated so that they may be mixed for use at the time of application, or they may be formulated together. The present invention includes such a mixed herbicidal composition.

The mixing ratio of the compound of the present invention to the active compounds of other herbicides can not generally be defined, since it varies depending upon the weather conditions, the soil conditions, the types of formulations, the application time, the application method, etc., but the other herbicides are mixed in an amount of from 0.001 to 10,000 parts by weight, preferably from 0.01 to 1,000 parts by weight per one type of the active compound, based on 1 part by weight of the compound of the present invention. Further, the dose for the application is such that the total amount of the active compounds is from 0.1 to 10,000 g, preferably from 0.2 to 5,000 g, more preferably from 10 to 3,000 g, per hectare. The present invention includes a method for controlling undesired weeds by application of such a mixed herbicidal composition.

Another herbicidally active compound includes, for example, the following compounds (common names including ones under application for approval by ISO). Even when not specifically mentioned here, in a case where such compounds have salts, alkyl esters, etc., they are, of course, all included.

(1) Those which are believed to exhibit herbicidal effects by disturbing hormone activities of plants, such as a phenoxy type such as 2,4-D, 2,4-DB, 2,4-DP, MCPA, MCPB, MCPP, naproanilide or clomeprop, an aromatic carboxylic acid type such as 2,3,6-TBA, dicamba, dichlobenil, picloram, triclopyr, clopyralid or aminopyralid, and others such as naptalam, benazolin, quinclorac, quinmerac, diflufenzopyr and thiazopyr.

(2) Those which are believed to exhibit herbicidal effects by inhibiting photosynthesis of plants, such as a urea type such as chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron or tebuthiuron, a triazine type such as simazine, atrazine, atratone, simetryn, prometryn, dimethametryn, hexazinone, metribuzin, terbuthylazine, cyanazine, ametryn, cybutryne, triaziflam or propazine, a uracil type such as bromacil, lenacil or terbacil, an anilide type such as propanil or cypromid, a carbamate type such as swep, desmedipham or phenmedipham, a hydroxybenzonitrile type such as bromoxynil, bromoxynil-octanoate or ioxynil, and others such as pyridate, bentazone, amicarbazone and methazole.

(3) Quaternary ammonium salt type such as paraquat or diquat, which is believed to be converted to free radicals by itself to form active oxygen in the plant body.

(4) Those which are believed to exhibit herbicidal, effects by inhibiting chlorophyll biosynthesis of plants and abnormally accumulating a photosensitizing peroxide substance in the plant body, such as a diphenylether type such as nitrofen, chlomethoxyfen, bifenox, acifluorfen-sodium, fomesafen, oxyfluorfen, lactofen or ethoxyfen-ethyl, a cyclic imide type such as chlorphthalim, flumioxazin, flumiclorac-pentyl or fluthiacet-methyl, and others such as oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone, azafenidin, isopropazole, pyraflufen-ethyl, benzfendizone, butafenacil, metobenzuron, cinidon-ethyl, flupoxam, fluazolate, profluazol, pyrachlonil, flufenpyr-ethyl and bencarbazone.

(5) Those which are believed to exhibit herbicidal, effects characterized by bleaching activities by inhibiting chromogenesis of plants such as carotenoids, such as a pyridazinone type such as norflurazon, chloridazon or metflurazon, a pyrazole type such as pyrazolate, pyrazoxyfen, benzofenap, topramezone (BAS-670H) or pyrasulfotole, and others such as amitrol, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulcotrione, mesotrione, tembotrione, tefuryltrione (AVH-301), isoxaflutole, difenzoquat, isoxachlortole, benzobicyclon, picolinafen and beflubutamid.

(6) Those which exhibit strong herbicidal effects specifically to gramineous plants, such as an aryloxyphenoxypropionic acid type such as diclofop-methyl, flamprop-M-methyl, pyriphenop-sodium, fluazifop-butyl, haloxyfop-methyl, quizalofop-ethyl, cyhalofop-butyl, fenoxaprop-ethyl or metamifop-propyl, and a cyclohexanedione type such as alloxydim-sodium, clethodim, sethoxydim, tralkoxydim, butroxydim, teptaloxydim, caloxydim, clefoxydim or profoxydim.

(7) Those which are believed to exhibit herbicidal effects by inhibiting an amino acid biosynthesis of plants, such as a sulfonylurea type such as chlorimuron-ethyl, sulfometuron-methyl, primisulfuron-methyl, bensulfuron-methyl, chlorsulfuron, metsulfuron-methyl, cinosulfuron, pyrazosulfuron-ethyl, azimsulfuron, flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron, cyclosulfamuron, prosulfuron, flupyrsulfuron, triflusulfuron-methyl, halosulfuron-methyl, thifensulfuron-methyl, ethoxysulfuron, oxasulfuron, ethametsulfuron, iodosulfuron, sulfosulfuron, triasulfuron, tribenuron-methyl, tritosulfuron, foramsulfuron, trifloxysulfuron, mesosulfuron-methyl, orthosulfamuron, flucetosulfuron, amidosulfuron, TH-547, a compound disclosed in WO2005092104, a triazolopyrimidinesulfonamide type such as flumetsulam, metosulam, diclosulam, cloransulam-methyl, florasulam, metosulfam or penoxsulam, an imidazolinone type such as imazapyr, imazethapyr, imazaquin, imazamox, imazameth, imazamethabenz or imazapic, a pyrimidinylsalicylic acid type such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid or pyrimisulfan (KUH-021), a sulfonylaminocarbonyltriazolinone type such as flucarbazone or procarbazone-sodium, and others such as glyphosate, glyphosate-sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-isopropylamine, sulfosate, glufosinate, glufosinate-ammonium and bilanafos.

(8) Those which are believed to exhibit herbicidal effects by inhibiting cell mitoses of plants, such as a dinitroaniline type such as trifluralin, oryzalin, nitralin, pendimethalin, ethalfluralin, benfluralin or prodiamine, an amide type such as bensulide, napronamide or pronamide, an organic phosphorus type such as amiprofos-methyl, butamifos, anilofos or piperophos, a phenylcarbamate type such as propham, chlorpropham or barban, a cumylamine type such as daimuron, cumyluron or bromobutide, and others such as asulam, dithiopyr and thiazopyr.

(9) Those which are believed to exhibit herbicidal effects by inhibiting protein biosynthesis or lipid biosynthesis of plants, such as a chloroacetamide type such as alachlor, metazachlor, butachlor, pretilachlor, metolachlor, S-metolachlor, thenylchlor, pethoxamid, acetochlor, propachloror propisochlor, a carbamate type such as molinate, dimepiperate or pyributicarb, and others such as etobenzanid, mefenacet, flufenacet, tridiphane, cafenstrole, fentrazamide, oxaziclomefone, indanofan, dimethenamid, benfuresate and pyroxasulfone (KIH-485).

(10) A thiocarbamate type such as EPTC, butylate, vernolate, pebulate, cycloate, prosulfocarb, esprocarb, thiobencarb, diallate or triallate, and others such as MSMA, DSMA, endothall, ethofumesate, sodium chlorate, pelargonic acid, fosamine, pinoxaden and HOK-201.

(11) Those which are believed to exhibit herbicidal effects by being parasitic on plants, such as Xanthomonas campestris, Epicoccosurus nematosurus, Exserohilum monoseras and Drechsrela monoceras.

Examples of preferred embodiments of the present invention are shown below, but the present invention is by no means restricted thereto.

(1) A benzoylpyrazole compound of the above formula (I), wherein R¹ is alkyl or cycloalkyl, R² is a hydrogen atom or alkyl, R³ is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl; alkenyl; or arylalkyl which may be substituted by R⁸, R⁴ is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R⁵ is a hydrogen atom; alkyl; halogen; cyano; cyanoalkyl; haloalkyl; alkoxyalkyl; haloalkoxyalkyl; alkoxy; haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy; alkoxyhaloalkoxy; alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio; haloalkoxyalkylthio; alkylthioalkylthio; haloalkylthioalkylthio; alkylthioalkoxy; alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl; alkoxycarbonylalkoxy; heterocyclyloxy; heterocyclylalkoxy; heterocyclylalkoxyalkyl; —OC(O)SR⁷; —OC(O)OR⁷; —C(O)OR⁷; —C(O)SR⁷; or 4,5-dihydroisoxazol-3-yl which may be substituted by R⁹, R⁶ is haloalkyl; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R⁷ is alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl which may be substituted by R¹⁰, and each of R⁸, R⁹ and R¹⁰ which are independent of one another, is halogen; alkyl; or alkoxy, or its salt, a process for producing it, a herbicide containing it as an active ingredient, and a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of it to the undesired plants or to a place where they grow. (2) A benzoylpyrazole compound of the above formula (I), wherein R¹ is alkyl or cycloalkyl, R² is a hydrogen atom or alkyl, R³ is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl; or arylalkyl which may be substituted by R⁸, R⁴ is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfony, R⁵ is alkyl; haloalkyl; alkoxyalkyl; haloalkoxyalkyl; alkoxy; haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy; heterocyclyloxy; heterocyclylalkoxy; heterocyclylalkoxyalkyl; —OC(O)SR⁷; —OC(O)OR⁷; —C(O)OR⁷; —C(O)SR⁷; or 4,5-dihydroisoxazol-3-yl which may be substituted by R⁹, R⁶ is haloalkyl; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R⁷ is alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl which may be substituted by R¹⁰, and each of R⁸, R⁹ and R¹⁰ which are independent of one another, is halogen; alkyl; or alkoxy, or its salt, a process for producing it, a herbicide containing it as an active ingredient, and a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of it to the undesired plants or to a place where they grow. (3) A benzoylpyrazole compound of the above formula (I) wherein R¹ is alkyl, R² is a hydrogen atom, R³ is alkyl, R⁴ is alkyl, R⁵ is alkoxy; haloalkoxy; —C(O)OR⁷; or 4,5-dihydroisoxazol-3-yl, and R⁵ is alkylsulfonyl, or its salt, a process for producing it, a herbicide containing it as an active ingredient, and a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of it to the undesired plants or to a place where they grow. (4) A mixed herbicidal composition containing the benzoylpyrazole compound of the above formula (I) or its salt, and one or more types of active compounds of other herbicides, and a method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of such a composition to, the undesired plants or to a place where they grow.

Now, the present invention will be described in detail with reference to Examples. However, it should be understood that the present invention is by no means restricted to such specific Examples.

Preparation examples for compounds of the present invention are described below.

Preparation Example 1 Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone (Compound No. 1 as Described Hereinafter)

5-Hydroxy-1-methylpyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone (290 mg, 0.82 mmol) was dissolved in dry tetrahydrofuran (15 mL), and triethylamine (166 mg, 1.64 mmol) was added thereto. A solution (4 mL) of 96% S-ethyl chlorothiolformate (107 mg) dissolved in dry tetrahydrofuran was added thereto little by little under cooling with ice water. The reaction mixture was stirred for 90 minutes while the reaction temperature was allowed to warm to room temperature. The reaction solution was poured into ice water, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4) to obtain the desired product as an amorphous solid (202 mg, 0.46 mmol) (yield: 56%).

Preparation Example 2 Preparation of 1-ethyl-5-(ethylthio)carbonyloxypyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone (Compound No. 2 as Described Hereinafter)

5-Hydroxy-1-ethylpyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone (510 mg, 1.39 mmol) was dissolved in dry tetrahydrofuran-(20 mL), and triethylamine (281 mg, 2.78 mmol) was added thereto. A solution (4 mL) of 96% S-ethyl chlorothiolformate (217 mg) dissolved in dry tetrahydrofuran was added thereto little by little under cooling with ice water. The reaction mixture was stirred for 90 minutes while the reaction temperature was allowed to warm to room temperature. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4) to obtain the desired product as an oil (417 mg, 0.92 mmol) (yield: 66%)

Preparation Example 3 Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-4-yl 3-(methoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (Compound No. 35 as Described Hereinafter)

(1) To a stirred mixture of 3-methoxy-2-methyl-4-(methylsulfonyl)benzoic acid (340 mg, 1.39 mmol) and 5-hydroxy-1-methylpyrazole hydrochloride (230 mg) in anhydrous methylene chloride (10 mL) were added DCC (dicyclohexylcarbodiimide) (315 mg) and triethylamine (260 mg) at room temperature, followed by stirring for 2 hours. The reaction mixture was subjected to filtration through Celite, the filtrate was concentrated, and the obtained residue was dissolved in 10 mL of anhydrous acetonitrile. Triethylamine (260 mg) and acetone cyanohydrin in a catalytic amount were added thereto, and the reaction solution was stirred overnight at room temperature. 150 mL of ethyl acetate was added, and the solution was washed once with a 1N hydrochloric acid aqueous solution and washed once with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1) to obtain 5-hydroxy-1-methylpyrazol-4-yl 3-methoxy-2-methyl-4-(methylsulfonyl)phenyl ketone (115 mg).

¹H-NMR (400 MHz CDCl₃ δ ppm): 2.31 (s, 3H), 3.20 (s, 3H) 3.66 (s, 3H), 3.92 (s, 3H), 7.1 (br s, 1H), 7.29 (d, 1H, J=7.6 Hz), 7.30 (s, 1H), 7.85 (d, 1H, J=7.6 Hz).

(2) To a solution of 5-hydroxy-1-methylpyrazol-4-yl 3-methoxy-2-methyl-4-(methylsulfonyl)phenyl ketone (100 mg, 0.3 mmol) in dry tetrahydrofuran (5 mL) were added triethylamine (61 mg) and 96% S-ethyl chlorothiolformate (50 mg) at room temperature. After the reaction solution was stirred for 1 hour, 150 mL of ethyl acetate was added. The mixture was washed twice with a saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product as an oil.

Preparation Example 4 Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-4-yl 2-methyl-4-(methylsulfonyl)-3-(4,5-dihydroisoxazol-3-yl)phenyl ketone (Compound No. 39 as Described Hereinafter)

To a solution of 5-hydroxy-1-methylpyrazol-4-yl 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)phenyl ketone (100 mg, 2.75×10⁻⁴ mol) in anhydrous tetrahydrofuran (5 mL) were added triethylamine (55 mg) and 96% S-ethyl chlorothiolformate (45 mg) at room temperature. After the reaction solution was stirred for 1 hour, 150 mL of ethyl acetate was added, and the solution was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4) to obtain the desired product (82 mg) as an oil.

Preparation Example 5 Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-4-yl 3-(difluoromethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (Compound No. 38 as Described Hereinafter)

(1) To a stirred mixture of 3-(difluoromethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (500 mg, 1.78 mmol) and 5-hydroxy-1-methylpyrazole hydrochloride (288 mg) in anhydrous acetonitrile (10 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (443 mg), triethylamine (360 mg) and dimethylaminopyridine (217 mg) at room temperature. After being stirred for 12 hours, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in 100 mL of methylene chloride. This solution was washed with 100 mL of water, and the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in 10 mL of anhydrous acetonitrile, and triethylamine (260 mg) and acetone cyanohydrin in a catalytic amount were added, followed by stirring overnight at room temperature. 150 mL of methylene chloride was added, followed by extraction with a 1N potassium carbonate aqueous solution, and the aqueous layer was acidified by 2N hydrochloric acid. The obtained acidic aqueous solution was extracted twice with methylene chloride (100 mL), the combined organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:1 to 9:1) to obtain 5-hydroxy-1-methylpyrazol-4-yl 3-(difluoromethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone as an oil.

¹H-NMR (400 MHz acetone-d₆ δ ppm): 2.37 (s, 3H), 3.28 (s, 3H), 3.61 (s, 3H), 6.90 (d, 1H, J=75.2 Hz), 7.27 (s, 1H), 7.59 (d, 1H, J=8.4 Hz), 7.96 (d, 1H, J=8.4 Hz).

(2) To a solution of 5-hydroxy-1-methylpyrazol-4-yl 3-(difluoromethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (89 mg) in dry tetrahydrofuran (5 mL) were added triethylamine (50 mg) and 96% S-ethyl chlorothiolformate (40 mg) at room temperature. After the reaction solution was stirred for 1 hour, 150 mL of ethyl acetate was added. The mixture was washed twice with a saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product as an oil.

Preparation Example 6 Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (Compound No. 55 as Described Hereinafter)

(1) To a stirred suspension of sodium hydride (60%, 22.0 mg, 5.32 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added methyl 3-hydroxy-2-methyl-4-(methylsulfonyl)benzoate (1 g, 4.09 mmol) under nitrogen atmosphere at room temperature. After stirring for 30 minutes, 2-bromoethyl methyl ether (1.13 g, 8.18 mmol) and potassium iodide in a catalytic amount were added thereto, and the reaction solution was stirred at 60° C. for 12 hours. 200 mL of ethyl acetate was added to the reaction solution, and the solution was washed twice with a saturate brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2) to obtain methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate as an oil (680 mg).

¹H-NMR 400 MHz (CDCl₃ δ ppm) 2.53 (s, 3H), 3.26 (s, 3H), 3.46 (s, 3H), 3.78 (m, 2H), 3.91 (s, 3H), 4.19 (m, 2H), 7.71 (d, 1H, J=8.4 Hz), 7.84 (d, 1H, J=8.4 Hz).

(2) Methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate (680 mg, 2.25 mmol) was dissolved in methanol (10 mL), and an aqueous sodium hydroxide solution (2 mL) at a concentration of 20% was added thereto at room temperature. After stirring for 30 minutes, the solvent was removed under reduced pressure. 100 mL of 1N hydrochloric acid was added to the residue, followed by extraction with ethyl acetate (200 mL). The organic layer was washed twice with a saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (570 mg) as a white solid.

¹H-NMR 400 MHz (acetone-d₆ δ ppm); 2.56 (s, 3H), 3.31 (s, 3H), 3.41 (s, 3H), 3.80 (m, 2H), 4.21 (m, 2H), 7.81 (s, 2H).

(3) To a solution of 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (195 mg, 6.76 mmol) in chloroform (15 mL) were added oxalyl-chloride (0.5 mL) and DMF in a catalytic amount. The reaction mixture was stirred for 30 minutes at room temperature, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous THF (20 mL), and 5-hydroxy-1-methylpyrazole hydrochloride (136 mg, 1.01 mmol), triethylamine (136 mg) and N,N-dimethylaminopyridine (250 mg) were added, followed by reflux with heating for 1 hour. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate (200 mL). The mixture was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous acetonitrile (10 mL), and triethylamine (136 mg) and acetone cyanohydrin in a catalytic amount were added. The mixture was stirred for 12 hours at room temperature. The solvent was distilled off under reduced pressure to obtain crude 5-hydroxy-1-methylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone.

¹H-NMR (400 MHz CDCl₃ δ ppm); 2.39 (s, 3H), 3.29 (s, 3H), 3.46 (s, 3H), 3.71 (s, 3H), 3.81 (m, 2H), 4.24 (m, 2H), 7.34 (s, 1H), 7.35 (d, 1H, J=7.6 Hz), 7.92 (d, 1H, J=7.6 Hz).

(4) The crude 5-hydroxy-1-methylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone obtained in the above step (3) was dissolved in anhydrous THF (10 mL), and triethylamine (190 mg) and 96% S-ethyl chlorothiolformate (151 mg) were added, followed by stirring for 1 hour at room temperature. Ethyl acetate (200 mL) was added to the reaction mixture, and the mixture was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the desired product (250 mg).

Preparation Example 7 Preparation of 5-(ethylthio)carbonyloxy-1-ethylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (Compound No. 16 as Described Hereinafter)

(1) To a solution of 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (200 mg, 6.90×10⁻⁴ mol) in chloroform (15 mL) were added oxalyl chloride (0.5 mL) and DMF in a catalytic amount. The reaction mixture was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous THF (20 mL), and 5-hydroxy-1-ethylpyrazole hydrochloride (134 mg, 9.01×10⁻⁴ mol), triethylamine (139 mg) and N,N-dimethylaminopyridine (170 mg) were added. The mixture was heated at refluxed temperature for 1 hour. The reaction mixture was allowed to cool to room temperature, and then ethyl acetate (200 mL) was added. The mixture was washed twice with a saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous acetonitrile (10 mL), and triethylamine (139 mg) and acetone cyanohydrin in a catalytic amount were added, followed by stirring for 12 hours at room temperature. The solvent was distilled off under reduced pressure to obtain crude 5-hydroxy-1-ethylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone.

¹H-NMR (400 MHz CDCl₃ δ ppm); 1.40 (t, 3H, J=7.0 Hz), 2.39 (s, 3H), 3.25 (s, 3H), 3.42 (s, 3H), 3.76 (m, 2H), 4.02 (q, 2H, J=7.0 Hz), 4.20 (m, 2H), 7.28 (s, 1H), 7.31 (d, 1H, J=7.6 Hz), 7.87 (d, 1H, J=7.6 Hz).

(2) The crude 5-hydroxy-1-ethylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone obtained in the above step (1) was dissolved in anhydrous THF (10 mL), and triethylamine (139 mg) and 96% S-ethyl chlorothiolformate (111 mg) were added, followed by stirring for 1 hour at room temperature. Ethyl acetate (200 mL) was added to the obtained reaction mixture, and the mixture was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the desired product (170 mg).

Preparation Example 8 Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-4-yl 3-(2,2-dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (Compound No. 209 as Described Hereinafter)

(1) 3-Hydroxy-2-methyl-4-(methylsulfonyl)benzoic acid (300 mg, 1.30 mmol) was dissolved in N,N-dimethylformamide (10 mL), and potassium carbonate (360 mg, 2.72 mmol) and bromoacetaldehyde dimethyl acetal (660 mg, 3.90 mmol) were added at room temperature. The reaction mixture was heated at 80° C., followed by stirring for 32 hours. The reaction mixture was allowed to cool to room temperature, and 100 mL of water and a 0.5N sodium hydroxide aqueous solution (10 mL) were added. Then, extraction with ethyl acetate (200 mL) was carried out, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 2,2-dimethoxyethyl 3-(2,2-dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate as an oil.

¹H-NMR 400 MHz (CDCl₃ δ ppm) 2.54 (s, 3H), 3.31 (s, 1H), 3.39 (s, 6H), 3.44 (s, 6H), 4.06 (d, 2H, J=5.4 Hz), 4.31 (d, 2H, J=5.4 Hz), 4.73 (t, 1H, J=5.4 Hz), 4.87 (t, 1H, J=5.4 Hz), 7.76 (d, 1H, J=8.4 Hz), 7.82 (d, 1H, J=8.4 Hz).

(2) The 2,2-dimethoxyethyl 3-(2,2-dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate obtained in the above step (1) was dissolved in methanol (20 mL), and an aqueous sodium hydroxide solution (2 mL) at a concentration of 20% was added thereto at room temperature. After stirring for 30 minutes, 100 mL of 1N hydrochloric acid was added to the reaction solution, followed by extraction with ethyl acetate. (200 mL). The organic layer was washed twice with a saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 3-(2,2-dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (390 mg) as a white solid.

¹H-NMR 400 MHz (acetone-d₆ δ ppm): 2.56 (s, 3H), 3.31 (s, 3H), 3.44 (s, 6H), 4.06 (d, 2H, J=5.2 Hz), 4.88 (t, 1H, J=5.2 Hz), 7.82 (br s, 2H).

(3) 3-(2,2-Dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (390 mg, 1.23 mmol) was dissolved in chloroform (15 mL), and oxalyl chloride (0.5 mL) and DMF in a catalytic amount were added thereto. The reaction mixture was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous THF (20 mL), and 5-hydroxy-1-methylpyrazole (132 mg, 1.35 mmol), triethylamine (250 mg) and N,N-dimethylaminopyridine (300 mg) were added, followed by reflux with heating for 1 hour. The reaction mixture was allowed to cool to room temperature, and ethyl acetate (200 mL) was added. The mixture was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous acetonitrile (10 mL), and triethylamine (250 mg) and acetone cyanohydrin in a catalytic amount were added, followed by stirring for 12 hours at room temperature. The solvent was distilled off under reduced pressure to obtain crude 5-hydroxy-1-methylpyrazol-4-yl 3-(2,2-dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone.

¹H-NMR (400 MHz CDCl₃ δ ppm): 2.38 (s, 3H), 3.29 (s, 3H), 3.47 (s, 6H), 3.70 (s, 3H), 4.09 (d, 2H, J=5.2 Hz), 4.1 (br s, 1H), 4.83 (t, 1H, J=5.2 Hz), 7.32 (s, 1H), 7.35 (d, 1H, J=8.4 Hz), 7.91 (d, 1H, J=8.4 Hz).

(4) The crude 5-hydroxy-1-methylpyrazol-4-yl 3-(2,2-dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone obtained in the above step (3) was dissolved in anhydrous THF (10 mL), and triethylamine (250 mg) and, 96% S-ethyl chlorothiolformate (200 mg) were added, followed by stirring for 1 hour at room temperature. Ethyl acetate (200 mL) was added to the obtained reaction mixture, and the mixture was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the desired product (150 mg).

Now, typical examples of the compounds of the present invention represented by the above formula (I) are shown in Table 1, and their ¹H-NMR spectrum data are shown in Table 2. Further, typical examples of the compounds represented by the formula (II) as intermediates for preparation of the compounds of the formula (I) are shown in Table 3, and their ¹H-NMR spectrum data are shown in Table 4. These compounds can be prepared in accordance with the above Preparation Examples or the above various processes for production of the compounds of the present invention. In Tables 1 to 4, No. represents the Compound No. In Tables 1 and 3, Me represents a methyl group, Et an ethyl group, n-Pr a normal-propyl group, i-Pr an isopropyl group, c-Pr a cyclopropyl group, s-Bu a secondary butyl group, t-Bu a tertiary butyl group, Ph a phenyl group, and Bn a benzyl group, respectively.

TABLE 1 (I)

No. R¹ R² R³ R⁴ R⁵ R⁶ 1 Me H Et Me CO₂Me SO₂Me 2 Et H Et Me CO₂Me SO₂Me 3 Me H Me Me CO₂Me SO₂Me 4 Et H Me Me CO₂Me SO₂Me 5 n-Pr H Et Me CO₂Me SO₂Me 6 c-Pr H Et Me CO₂Me SO₂Me 7 n-Pr H Me Me CO₂Me SO₂Me 8 c-Pr H Me Me CO₂Me SO₂Me 9 t-Bu H Et Me CO₂Me SO₂Me 10 t-Bu H Me Me CO₂Me SO₂Me 11 Me Me Et Me CO₂Me SO₂Me 12 Et H Et Me CO₂(i-Pr) SO₂Me 13 Me H Et Me CO₂Et SO₂Me 14 Et H Et Me CO₂Me NO₂ 15 Et H Et SO₂Me CO₂Me CF₃ 16 Et H Et Me OCH₂CH₂OMe SO₂Me 17 Et H Et Cl OCH₂CH₂OMe SO₂Me 18 Et H Et Me CO₂Me CN 19 Me H Et Me C(O)SMe SO₂Me 20 Et H Et Me C(O)SMe SO₂Me 21 Me H Me Me C(O)SEt SO₂Me 22 Et H Me Me C(O)SEt SO₂Me 23 Me H Et Me 2-(2-oxolanyl)ethoxy SO₂Me 24 Me H Et Me 2-(2-(1,3-dioxolanyl))-ethoxy SO₂Me 25 Et H Et Me CH₂OMe SO₂Me 26 Et H Et Me 2-oxolanylmethoxymethyl SO₂Me 27 Me H Et Cl CO₂Me SO₂Me 28 Et H Et Cl CO₂Me SO₂Et 29 Me H Me Cl CO₂Me SO₂Me 30 Et H Me Br CO₂Me SO₂Me 31 Me H Et Cl C(O)SMe SO₂Me 32 Et H Et Cl C(O)SMe SO₂Me 33 Me H Et Cl C(O)SEt SO₂Me 34 Et H Et Cl C(O)SEt SO₂Me 35 Me H Et Me OMe SO₂Me 36 Me H Et Me OEt SO₂Me 37 Me H Et Me O(i-Pr) SO₂Me 38 Me H Et Me OCHF₂ SO₂Me 39 Me H Et Me (4,5-dihydroisoxazol-3-yl) SO₂Me 40 Me H Me Me (4,5-dihydroisoxazol-3-yl) SO₂Me 41 Me H Et Me O(n-Pr) SO₂Et 42 Me H Et Cl CH₂OMe SO₂Me 43 Me H Et Me OCO₂Me SO₂Me 44 Et H Et Me OCO₂Me SO₂Me 45 Me H Me Me OCO₂Me SO₂Me 46 Et H Me Me OCO₂Me SO₂Me 47 Me H Et Me OC(O)SMe SO₂Me 48 Et H Et Me OC(O)SMe SO₂Me 49 Me H Me Me OC(O)SMe SO₂Me 50 Et H Me Me OC(O)SMe SO₂Me 51 Me H Et Me OC(O)SEt SO₂Me 52 Et H Et Me OC(O)SEt SO₂Me 53 Me H Me Me OC(O)SEt SO₂Me 54 Et H Me Me OC(O)SEt SO₂Me 55 Me H Et Me OCH₂CH₂OMe SO₂Me 56 Me H Me Me OCH₂CH₂OMe SO₂Et 57 Me H Et Cl OCH₂CH₂OMe SO₂Me 58 Et H Et Me OEt SO₂Me 59 Et H Et Cl CO₂Et SO₂Me 60 Et H Et Cl CO₂(n-Pr) SO₂Me 61 Et H Et Me CO₂Et SO₂Me 62 Et H Me Me CO₂Et SO₂Me 63 Me H Et Me CH₂OMe SO₂Me 64 Me H Et Me CH₂CO₂Me SO₂Me 65 Me H Et Me OCH₂CO₂Et SO₂Me 66 Me H Et Me O(n-Pr) SO₂Me 67 Et H Et Me O(n-Pr) SO₂Me 68 Et H Et SO₂Me H CF₃ 69 Me H Et Me CH₂OCH₂CF₃ SO₂Me 70 Me H Et Cl CH₂OCH₂CF₃ SO₂Me 71 Et H Et Me Cl SO₂Me 72 Me H Et Me CH₂SO₂Me SO₂Me 73 Me H Et Me CH₂OEt SO₂Me 74 Me H Me Cl CH₂OMe SO₂Me 75 Me H Et Me CH₂CH₂OMe SO₂Me 76 Me H Et Me CH₂OCH₂CH₂OMe SO₂Me 77 Me H Et Me OCH₂CH₂OEt SO₂Me 78 Me H Et Me OCH₂CH₂Cl SO₂Me 79 Me H Et Me OCH₂CF₃ SO₂Me 80 Me H Et Me CH₂OCH₂OMe SO₂Me 81 Me H Et Me OCH₂CH₂SMe SO₂Me 82 Me H Et Me CN SO₂Me 83 Me H Et Me CH₂CN SO₂Me 84 Me H n-Pr Me CO₂Me SO₂Me 85 Et H n-Pr Me CO₂Me SO₂Me 86 Me H i-Pr Me CO₂Me SO₂Me 87 Et H i-Pr Me CO₂Me SO₂Me 88 Me H s-Bu Me CO₂Me SO₂Me 89 Et H s-Bu Me CO₂Me SO₂Me 90 Me H t-Bu Me CO₂Me SO₂Me 91 Et H t-Bu Me CO₂Me SO₂Me 92 Me H Bn Me CO₂Me SO₂Me 93 Et H Bn Me CO₂Me SO₂Me 94 Me H Et Br CO₂Me SO₂Me 95 Et H Et Cl CO₂Me SO₂Me 96 Me H Me Br CO₂Me SO₂Me 97 Et H Me Cl CO₂Me SO₂Me 98 Me H Allyl Me CO₂Me SO₂Me 99 Et H Allyl Me CO₂Me SO₂Me 100 Me H CH₂CH(CH₃)═CH₂ Me CO₂Me SO₂Me 101 Et H CH₂CH(CH₃)═CH₂ Me CO₂Me SO₂Me 102 Me H Et Cl OCH₂CH₂OCF₃ SO₂Me 103 Et H Et Cl OCH₂CH₂OCF₃ SO₂Me 104 Me H Et Me OCH₂CH₂OCF₃ SO₂Me 105 Et H Et Me OCH₂CH₂OCF₃ SO₂Me 106 Me H Et CF₃ OCH₂CH₂OCF₃ SO₂Me 107 Et H Et CF₃ OCH₂CH₂OCF₃ SO₂Me 108 Me H Et Br OCH₂CH₂OCF₃ SO₂Me 109 Et H Et Br OCH₂CH₂OCF₃ SO₂Me 110 Me H Et SO₂Me OCH₂CH₂OCF₃ CF₃ 111 Et H Et SO₂Me OCH₂CH₂OCF₃ CF₃ 112 Me H Et Cl OCH₂CH₂OCHClF SO₂Me 113 Et H Et Cl OCH₂CH₂OCHClF SO₂Me 114 Me H Et Me OCH₂CH₂OCHClF SO₂Me 115 Et H Et Me OCH₂CH₂OCHClF SO₂Me 116 Me H Et CF₃ OCH₂CH₂OCHClF SO₂Me 117 Et H Et CF₃ OCH₂CH₂OCHClF SO₂Me 118 Me H Et Br OCH₂CH₂OCHClF SO₂Me 119 Et H Et Br OCH₂CH₂OCHClF SO₂Me 120 Me H Et SO₂Me OCH₂CH₂OCHClF CF₃ 121 Et H Et SO₂Me OCH₂CH₂OCHClF CF₃ 122 Me H Et Cl OCH₂CHFOCF₃ SO₂Me 123 Et H Et Cl OCH₂CHFOCF₃ SO₂Me 124 Me H Et Me OCH₂CHFOCF₃ SO₂Me 125 Me H Et Cl OCH₂CHFOMe SO₂Me 126 Et H Et Cl OCH₂CHFOMe SO₂Me 127 Me H Et Me OCH₂CHFOMe SO₂Me 128 Et H Et Me OCH₂CHFOMe SO₂Me 129 Me H Et CF₃ OCH₂CHFOMe SO₂Me 130 Et H Et CF₃ OCH₂CHFOMe SO₂Me 131 Me H Et Br OCH₂CHFOMe SO₂Me 132 Et H Et Br OCH₂CHFOMe SO₂Me 133 Me H Et SO₂Me OCH₂CHFOMe CF₃ 134 Et H Et SO₂Me OCH₂CHFOMe CF₃ 135 Me H Et Cl OCHFCH₂OCF₃ SO₂Me 136 Et H Et Cl OCHFCH₂OCF₃ SO₂Me 137 Me H Et Cl OCH₂CH₂OCF₂Cl SO₂Me 138 Et H Et Cl OCH₂CH₂OCF₂Cl SO₂Me 139 Me H Et Me OCH₂CH₂OCF₂Cl SO₂Me 140 Et H Et Me OCH₂CH₂OCF₂Cl SO₂Me 141 Me H Et CF₃ OCH₂CH₂OCF₂Cl SO₂Me 142 Et H Et CF₃ OCH₂CH₂OCF₂Cl SO₂Me 143 Me H Et Br OCH₂CH₂OCF₂Cl SO₂Me 144 Et H Et Br OCH₂CH₂OCF₂Cl SO₂Me 145 Me H Et SO₂Me OCH₂CH₂OCF₂Cl CF₃ 146 Et H Et SO₂Me OCH₂CH₂OCF₂Cl CF₃ 147 Me H Et Cl SCH₂CH₂OCH₃ SO₂Me 148 Et H Et Cl SCH₂CH₂OCH₃ SO₂Me 149 Me H Et Me SCH₂CH₂OCH₃ SO₂Me 150 Et H Et Me SCH₂CH₂OCH₃ SO₂Me 151 Me H Et CF₃ SCH₂CH₂OCH₃ SO₂Me 152 Et H Et CF₃ SCH₂CH₂OCH₃ SO₂Me 153 Me H Et Br SCH₂CH₂OCH₃ SO₂Me 154 Et H Et Br SCH₂CH₂OCH₃ SO₂Me 155 Me H Et SO₂Me SCH₂CH₂OCH₃ CF₃ 156 Et H Et SO₂Me SCH₂CH₂OCH₃ CF₃ 157 Me H Et Cl SCH₂CH₂OCF₃ SO₂Me 158 Et H Et Cl SCH₂CH₂OCF₃ SO₂Me 159 Me H Et Me SCH₂CH₂OCF₃ SO₂Me 160 Et H Et Me SCH₂CH₂OCF₃ SO₂Me 161 Me H Et CF₃ SCH₂CH₂OCF₃ SO₂Me 162 Et H Et CF₃ SCH₂CH₂OCF₃ SO₂Me 163 Me H Et Br SCH₂CH₂OCF₃ SO₂Me 164 Et H Et Br SCH₂CH₂OCF₃ SO₂Me 165 Me H Et SO₂Me SCH₂CH₂OCF₃ CF₃ 166 Et H Et SO₂Me SCH₂CH₂OCF₃ CF₃ 167 Me H Et Cl SCH₂CH₂SCH₃ SO₂Me 168 Et H Et Cl SCH₂CH₂SCH₃ SO₂Me 169 Me H Et Me SCH₂CH₂SCH₃ SO₂Me 170 Et H Et Me SCH₂CH₂SCH₃ SO₂Me 171 Me H Et CF₃ SCH₂CH₂SCH₃ SO₂Me 172 Et H Et CF₃ SCH₂CH₂SCH₃ SO₂Me 173 Me H Et Br SCH₂CH₂SCH₃ SO₂Me 174 Et H Et Br SCH₂CH₂SCH₃ SO₂Me 175 Me H Et SO₂Me SCH₂CH₂SCH₃ CF₃ 176 Et H Et SO₂Me SCH₂CH₂SCH₃ CF₃ 177 Me H Et Cl SCH₂CH₂SCF₃ SO₂Me 178 Et H Et Cl SCH₂CH₂SCF₃ SO₂Me 179 Me H Et Me SCH₂CH₂SCF₃ SO₂Me 180 Et H Et Me SCH₂CH₂SCF₃ SO₂Me 181 Me H Et CF₃ SCH₂CH₂SCF₃ SO₂Me 182 Et H Et CF₃ SCH₂CH₂SCF₃ SO₂Me 183 Me H Et Br SCH₂CH₂SCF₃ SO₂Me 184 Et H Et Br SCH₂CH₂SCF₃ SO₂Me 185 Me H Et SO₂Me SCH₂CH₂SCF₃ CF₃ 186 Et H Et SO₂Me SCH₂CH₂SCF₃ CF₃ 187 Me H Et Cl OCH₂CH(CH₃)OCH₃ SO₂Me 188 Et H Et Cl OCH₂CH(CH₃)OCH₃ SO₂Me 189 Me H Et Me OCH₂CH(CH₃)OCH₃ SO₂Me 190 Et H Et Me OCH₂CH(CH₃)OCH₄ SO₂Me 191 Me H Et CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 192 Et H Et CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 193 Me H Et Br OCH₂CH(CH₃)OCH₃ SO₂Me 194 Et H Et Br OCH₂CH(CH₃)OCH₃ SO₂Me 195 Me H Et SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 196 Et H Et SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 197 Me H Et Cl OCH₂CF₂OCH₃ SO₂Me 198 Et H Et Cl OCH₂CF₂OCH₃ SO₂Me 199 Me H Et Me OCH₂CF₂OCH₃ SO₂Me 200 Et H Et Me OCH₂CF₂OCH₃ SO₂Me 201 Me H Et CF₃ OCH₂CF₂OCH₃ SO₂Me 202 Et H Et CF₃ OCH₂CF₂OCH₃ SO₂Me 203 Me H Et Br OCH₂CF₂OCH₃ SO₂Me 204 Et H Et Br OCH₂CF₂OCH₃ SO₂Me 205 Me H Et SO₂Me OCH₂CF₂OCH₃ CF₃ 206 Et H Et SO₂Me OCH₂CF₂OCH₃ CF₃ 207 Me H i-Pr Me OCH₂CH₂OCH₃ SO₂Me 208 Et H i-Pr Me OCH₂CH₂OCH₃ SO₂Me 209 Me H Et Me OCH₂CH(OCH₃)₂ SO₂Me 210 Me H Et Me CH₂N(Me)CH₂CN SO₂Me 211 Me H Et Me (tetrahydrofuran-2-yl)methoxy SO₂Me 212 Me H Et Cl SMe SO₂Me 213 Me H Et Cl Cl SO₂Me 214 Me H Et Cl OMe SO₂Me 215 Me H Et Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 216 Me H Et Cl OCH₂CH₂OMe SO₂Me 217 Me H Et Me tetrahydrofuran-3-yloxy SO₂Me 218 Me H Et Me OCH₂CH₂CH₂OMe SO₂Me 219 Me H n-Pr Me OCH₂CH₂OMe SO₂Me 220 Et H s-Bu Cl C(O)OMe SO₂Me 221 Et H Et Cl 2-(1,3-dioxolan-2-yl)ethoxy SO₂Me 222 Me H Et Me propargyloxy SO₂Me 223 Me H Et Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 224 Me H Et Cl SO₂Me SO₂Me 225 Me H Et Me (CH₂)₆Me SO₂Me 226 Me H Et Me CH₂CH₂CH₂OMe SO₂Me 227 Et H Et Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 228 Me H Et Me CH₂N[C(O)SEt]CH₂CN SO₂Me 229 Me H Et Me CH═CHCN SO₂Me 230 Me H Et Me CH₂CH₂CN SO₂Me 231 Me H Et Me CH₂SCN SO₂Me 232 Me H Et Me CH₂C(S)NH₂ SO₂Me 233 Me H Me Me OCH₂CH₂OMe SO₂Me 234 Et H Me Me OCH₂CH₂OMe SO₂Me 235 Et H n-Pr Me OCH₂CH₂OMe SO₂Me 236 Me H Et Me OCH(CH₃)CH₂OMe SO₂Me 237 Et H Et Me OCH₂CH(Et)OMe SO₂Me 238 Me H Et Me (1,3-dioxolan-2-yl)methyl SO₂Me 239 Me H s-Bu Me OCH₂CH₂OMe SO₂Me 240 Me H Et Me CH₂O(i-Pr) SO₂Me 241 Me H t-Bu Me OCH₂CH₂OMe SO₂Me 242 Me H CH₂CO₂Me Me OCH₂CH₂OMe SO₂Me 243 Et H c-Pr Me CO₂Me SO₂Me 244 Et H c-Pr Me CO₂(i-Pr) SO₂Me 245 Et H c-Pr Me OCH₂CH₂OMe SO₂Me 246 Et H c-Pr SO₂Me CO₂Me CN 247 Me H c-Pr Me C(O)SMe SO₂Me 248 Me H c-Pr Me C(O)SEt SO₂Me 249 Me H c-Pr Me 2-(2-oxolanyl)ethoxy SO₂Me 250 Me H c-Pr Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 251 Et H c-Pr Me CH₂OMe SO₂Me 252 Et H c-Pr Me 2-oxolanylmethoxymethyl SO₂Me 253 Me H c-Pr Cl CO₂Me SO₂Me 254 Et H c-Pr Cl CO₂Me SO₂Et 255 Me H c-Pr Cl C(O)SMe SO₂Me 256 Me H c-Pr Cl C(O)SEt SO₂Me 257 Me H c-Pr Me OMe SO₂Me 258 Me H c-Pr Me OEt SO₂Me 259 Me H c-Pr Me O(i-Pr) SO₂Me 260 Me H c-Pr Me OCHF₂ SO₂Me 261 Me H c-Pr Me (4,5-dihydroisoxazol-3-yl) SO₂Me 262 Me H c-Pr Me O(n-Pr) SO₂Et 263 Me H c-Pr Cl CH₂OMe SO₂Me 264 Me H c-Pr Me OCO₂Me SO₂Me 265 Me H c-Pr Me OC(O)SMe SO₂Me 266 Me H c-Pr Me OC(O)SEt SO₂Me 267 Me H c-Pr Me OCH₂CH₂OMe SO₂Me 268 Et H c-Pr Me OEt SO₂Me 269 Et H c-Pr Cl CO₂Et SO₂Me 270 Et H c-Pr Cl CO₂(n-Pr) SO₂Me 271 Et H c-Pr Me CO₂Et SO₂Me 272 Me H c-Pr CN CO₂Me SO₂Me 273 Et H c-Pr CN CO₂(i-Pr) SO₂Me 274 Me H c-Pr Me CH₂CO₂Me SO₂Me 275 Me H c-Pr Me OCH₂CO₂Et SO₂Me 276 Me H c-Pr Me O(n-Pr) SO₂Me 277 Et H c-Pr SO₂Me H CF₃ 278 Me H c-Pr Me CH₂OCH₂CF₃ SO₂Me 279 Me H c-Pr Cl CH₂OCH₂CF₃ SO₂Me 280 Et H c-Pr Me Cl SO₂Me 281 Me H c-Pr Me CH₂SO₂Me SO₂Me 282 Me H c-Pr Me CH₂OEt SO₂Me 283 Me H c-Pr Cl CH₂OMe SO₂Me 284 Me H c-Pr Me CH₂CH₂OMe SO₂Me 285 Me H c-Pr Me CH₂OCH₂CH₂OMe SO₂Me 286 Me H c-Pr Me OCH₂CH₂OEt SO₂Me 287 Me H c-Pr Me OCH₂CH₂Cl SO₂Me 288 Me H c-Pr Me OCH₂CF₃ SO₂Me 289 Me H c-Pr Me CH₂OCH₂OMe SO₂Me 290 Me H c-Pr Me OCH₂CH₂SMe SO₂Me 291 Me H c-Pr Me CN SO₂Me 292 Me H c-Pr Me CH₂CN SO₂Me 293 Me H c-Pr Br CO₂Me SO₂Me 294 Et H c-Pr Cl CO₂Me SO₂Me 295 Me H c-Pr Br CO₂Et SO₂Me 296 Me H c-Pr Cl OCH₂CH₂OCF₃ SO₂Me 297 Et H c-Pr Cl OCH₂CH₂OCF₃ SO₂Me 298 Me H c-Pr Me OCH₂CH₂OCF₃ SO₂Me 299 Et H c-Pr Me OCH₂CH₂OCF₃ SO₂Me 300 Me H c-Pr CF₃ OCH₂CH₂OCF₃ SO₂Me 301 Et H c-Pr CF₃ OCH₂CH₂OCF₃ SO₂Me 302 Me H c-Pr Br OCH₂CH₂OCF₃ SO₂Me 303 Et H c-Pr Br OCH₂CH₂OCF₃ SO₂Me 304 Me H c-Pr SO₂Me OCH₂CH₂OCF₃ CF₃ 305 Et H c-Pr SO₂Me OCH₂CH₂OCF₃ CF₃ 306 Me H c-Pr Cl OCH₂CH₂OCHClF SO₂Me 307 Et H c-Pr Cl OCH₂CH₂OCHClF SO₂Me 308 Me H c-Pr Me OCH₂CH₂OCHClF SO₂Me 309 Et H c-Pr Me OCH₂CH₂OCHClF SO₂Me 310 Me H c-Pr CF₃ OCH₂CH₂OCHClF SO₂Me 311 Et H c-Pr CF₃ OCH₂CH₂OCHClF SO₂Me 312 Me H c-Pr Br OCH₂CH₂OCHClF SO₂Me 313 Et H c-Pr Br OCH₂CH₂OCHClF SO₂Me 314 Me H c-Pr SO₂Me OCH₂CH₂OCHClF CF₃ 315 Et H c-Pr SO₂Me OCH₂CH₂OCHClF CF₃ 316 Me H c-Pr Cl OCH₂CHFOCF₃ SO₂Me 317 Et H c-Pr Cl OCH₂CHFOCF₃ SO₂Me 318 Me H c-Pr Me OCH₂CHFOCF₃ SO₂Me 319 Me H c-Pr Cl OCH₂CHFOMe SO₂Me 320 Et H c-Pr Cl OCH₂CHFOMe SO₂Me 321 Me H c-Pr Me OCH₂CHFOMe SO₂Me 322 Et H c-Pr Me OCH₂CHFOMe SO₂Me 323 Me H c-Pr CF₃ OCH₂CHFOMe SO₂Me 324 Et H c-Pr CF₃ OCH₂CHFOMe SO₂Me 325 Me H c-Pr Br OCH₂CHFOMe SO₂Me 326 Et H c-Pr Br OCH₂CHFOMe SO₂Me 327 Me H c-Pr SO₂Me OCH₂CHFOMe CF₃ 328 Et H c-Pr SO₂Me OCH₂CHFOMe CF₃ 329 Me H c-Pr Cl OCHFCH₂OCF₃ SO₂Me 330 Et H c-Pr Cl OCHFCH₂OCF₃ SO₂Me 331 Me H c-Pr Cl OCH₂CH₂OCF₂Cl SO₂Me 332 Et H c-Pr Cl OCH₂CH₂OCF₂Cl SO₂Me 333 Me H c-Pr Me OCH₂CH₂OCF₂Cl SO₂Me 334 Me H c-Pr CN OCH₂CH₂OCF₃ SO₂Me 335 Et H c-Pr Me OCH₂CH₂OCF₂Cl SO₂Me 336 Me H c-Pr CF₃ OCH₂CH₂OCF₂Cl SO₂Me 337 Et H c-Pr CF₃ OCH₂CH₂OCF₂Cl SO₂Me 338 Me H c-Pr Br OCH₂CH₂OCF₂Cl SO₂Me 339 Et H c-Pr Br OCH₂CH₂OCF₂Cl SO₂Me 340 Me H c-Pr SO₂Me OCH₂CH₂OCF₂Cl CF₃ 341 Et H c-Pr SO₂Me OCH₂CH₂OCF₂Cl CF₃ 342 Me H c-Pr Cl SCH₂CH₂OCH₃ SO₂Me 343 Et H c-Pr Cl SCH₂CH₂OCH₃ SO₂Me 344 Me H c-Pr Me SCH₂CH₂OCH₃ SO₂Me 345 Et H c-Pr Me SCH₂CH₂OCH₃ SO₂Me 346 Me H c-Pr CF₃ SCH₂CH₂OCH₃ SO₂Me 347 Et H c-Pr CF₃ SCH₂CH₂OCH₃ SO₂Me 348 Me H c-Pr Br SCH₂CH₂OCH₃ SO₂Me 349 Et H c-Pr Br SCH₂CH₂OCH₃ SO₂Me 350 Me H c-Pr SO₂Me SCH₂CH₂OCH₃ CF₃ 351 Et H c-Pr SO₂Me SCH₂CH₂OCH₃ CF₃ 352 Me H c-Pr Cl SCH₂CH₂OCF₃ SO₂Me 353 Et H c-Pr Cl SCH₂CH₂OCF₃ SO₂Me 354 Me H c-Pr Me SCH₂CH₂OCF₃ SO₂Me 355 Et H c-Pr Me SCH₂CH₂OCF₃ SO₂Me 356 Me H c-Pr CF₃ SCH₂CH₂OCF₃ SO₂Me 357 Et H c-Pr CF₃ SCH₂CH₂OCF₃ SO₂Me 358 Me H c-Pr Br SCH₂CH₂OCF₃ SO₂Me 359 Et H c-Pr Br SCH₂CH₂OCF₃ SO₂Me 360 Me H c-Pr SO₂Me SCH₂CH₂OCF₃ CF₃ 361 Et H c-Pr SO₂Me SCH₂CH₂OCF₃ CF₃ 362 Me H c-Pr Cl SCH₂CH₂SCH₃ SO₂Me 363 Et H c-Pr Cl SCH₂CH₂SCH₃ SO₂Me 364 Me H c-Pr Me SCH₂CH₂SCH₃ SO₂Me 365 Et H c-Pr Me SCH₂CH₂SCH₃ SO₂Me 366 Me H c-Pr CF₃ SCH₂CH₂SCH₃ SO₂Me 367 Et H c-Pr CF₃ SCH₂CH₂SCH₃ SO₂Me 368 Me H c-Pr Br SCH₂CH₂SCH₃ SO₂Me 369 Et H c-Pr Br SCH₂CH₂SCH₃ SO₂Me 370 Me H c-Pr SO₂Me SCH₂CH₂SCH₃ CF₃ 371 Et H c-Pr SO₂Me SCH₂CH₂SCH₃ CF₃ 372 Me H c-Pr Cl SCH₂CH₂SCF₃ SO₂Me 373 Et H c-Pr Cl SCH₂CH₂SCF₃ SO₂Me 374 Me H c-Pr Me SCH₂CH₂SCF₃ SO₂Me 375 Et H c-Pr Me SCH₂CH₂SCF₃ SO₂Me 376 Me H c-Pr CF₃ SCH₂CH₂SCF₃ SO₂Me 377 Et H c-Pr CF₃ SCH₂CH₂SCF₃ SO₂Me 378 Me H c-Pr Br SCH₂CH₂SCF₃ SO₂Me 379 Et H c-Pr Br SCH₂CH₂SCF₃ SO₂Me 380 Me H c-Pr SO₂Me SCH₂CH₂SCF₃ CF₃ 381 Et H c-Pr SO₂Me SCH₂CH₂SCF₃ CF₃ 382 Me H c-Pr Cl OCH₂CH(CH₃)OCH₃ SO₂Me 383 Et H c-Pr Cl OCH₂CH(CH₃)OCH₃ SO₂Me 384 Me H c-Pr Me OCH₂CH(CH₃)OCH₃ SO₂Me 385 Et H c-Pr Me OCH₂CH(CH₃)OCH₃ SO₂Me 386 Me H c-Pr CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 387 Et H c-Pr CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 388 Me H c-Pr Br OCH₂CH(CH₃)OCH₃ SO₂Me 389 Et H c-Pr Br OCH₂CH(CH₃)OCH₃ SO₂Me 390 Me H c-Pr SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 391 Et H c-Pr SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 392 Me H c-Pr Cl OCH₂CF₂OCH₃ SO₂Me 393 Et H c-Pr Cl OCH₂CF₂OCH₃ SO₂Me 394 Me H c-Pr Me OCH₂CF₂OCH₃ SO₂Me 395 Et H c-Pr Me OCH₂CF₂OCH₃ SO₂Me 396 Me H c-Pr CF₃ OCH₂CF₂OCH₃ SO₂Me 397 Et H c-Pr CF₃ OCH₂CF₂OCH₃ SO₂Me 398 Me H c-Pr Br OCH₂CF₂OCH₃ SO₂Me 399 Et H c-Pr Br OCH₂CF₂OCH₃ SO₂Me 400 Me H c-Pr SO₂Me OCH₂CF₂OCH₃ CF₃ 401 Et H c-Pr SO₂Me OCH₂CF₂OCH₃ CF₃ 402 Me H c-Pr Me OCH₂CH₂OCH₃ SO₂Me 403 Et H c-Pr Me OCH₂CH₂OCH₃ SO₂Me 404 Me H c-Pr Me OCH₂CH(OCH₃)₂ SO₂Me 405 Me H c-Pr Me CH₂N(Me)CH₂CN SO₂Me 406 Me H c-Pr Me (tetrahydrofuran-2-yl)methoxy SO₂Me 407 Me H c-Pr Cl SMe SO₂Me 408 Me H c-Pr Cl Cl SO₂Me 409 Me H c-Pr Cl OMe SO₂Me 410 Me H c-Pr Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 411 Me H c-Pr Cl OCH₂CH₂OMe SO₂Me 412 Me H c-Pr Me tetrahydrofuran-3-yloxy SO₂Me 413 Me H c-Pr Me OCH₂CH₂CH₂OMe SO₂Me 414 Me H c-Pr CN OCH₂CH₂OMe SO₂Me 415 Et H c-Pr Cl 2-(1,3-dioxolan-2-yl)ethoxy SO₂Me 416 Me H c-Pr Me propargyloxy SO₂Me 417 Me H c-Pr Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 418 Me H c-Pr Cl SO₂Me SO₂Me 419 Me H c-Pr Me (CH₂)₆Me SO₂Me 420 Me H c-Pr Me CH₂CH₂CH₂OMe SO₂Me 421 Et H c-Pr Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 422 Me H c-Pr Me CH₂N[C(O)SEt]CH₂CN SO₂Me 423 Me H c-Pr Me CH═CHCN SO₂Me 424 Me H c-Pr Me CH₂CH₂CN SO₂Me 425 Me H c-Pr Me CH₂SCN SO₂Me 426 Me H c-Pr Me CH₂C(S)NH₂ SO₂Me 427 Me H c-Pr NO₂ OCH₂CH₂OMe SO₂Me 428 Et H c-Pr NO₂ OCH₂CH₂OMe SO₂Me 429 Me H c-Pr Me OCH(CH₃)CH₂OMe SO₂Me 430 Et H c-Pr Me OCH₂CH(Et)OMe SO₂Me 431 Me H c-Pr Me (1,3-dioxolan-2-yl)methyl SO₂Me 432 Me H c-Pr Me CH₂O(i-Pr) SO₂Me 433 Et H s-Bu Me CO₂(i-Pr) SO₂Me 434 Me H s-Bu Cl CO₂Et SO₂Me 435 Et H s-Bu Me CO₂Me CF₃ 436 Et H s-Bu Me OCH₂CH₂OMe SO₂Me 437 Et H s-Bu SO₂Me CO₂Me CN 438 Me H s-Bu Me C(O)SMe SO₂Me 439 Me H s-Bu Me C(O)SEt SO₂Me 440 Me H s-Bu Me 2-(2-oxolanyl)ethoxy SO₂Me 441 Me H s-Bu Me 2-(2-(1,3-dioxolanyl)ethoxy SO₂Me 442 Et H s-Bu Me CH₂OMe SO₂Me 443 Et H s-Bu Me 2-oxolanylmethoxymethyl SO₂Me 444 Me H s-Bu Cl CO₂Me SO₂Me 445 Et H s-Bu Cl CO₂Me SO₂Et 446 Me H s-Bu Cl C(O)SMe SO₂Me 447 Me H s-Bu Cl C(O)SEt SO₂Me 448 Me H s-Bu Me OMe SO₂Me 449 Me H s-Bu Me OEt SO₂Me 450 Me H s-Bu Me O(i-Pr) SO₂Me 451 Me H s-Bu Me OCHF₂ SO₂Me 452 Me H s-Bu Me (4,5-dihydroisoxazol-3-yl) SO₂Me 453 Me H s-Bu Me O(n-Pr) SO₂Et 454 Me H s-Bu Cl CH₂OMe SO₂Me 455 Me H s-Bu Me OCO₂Me SO₂Me 456 Me H s-Bu Me OC(O)SMe SO₂Me 457 Me H s-Bu Me OC(O)SEt SO₂Me 458 Et H s-Bu Me OEt SO₂Me 459 Et H s-Bu Cl CO₂Et SO₂Me 460 Et H s-Bu Cl CO₂(n-Pr) SO₂Me 461 Et H s-Bu Me CO₂Et SO₂Me 462 Me H s-Bu Me CH₂CO₂Me SO₂Me 463 Me H s-Bu Me OCH₂CO₂Et SO₂Me 464 Me H s-Bu Me O(n-Pr) SO₂Me 465 Et H s-Bu SO₂Me H CF₃ 466 Me H s-Bu Me CH₂OCH₂CF₃ SO₂Me 467 Me H s-Bu Cl CH₂OCH₂CF₃ SO₂Me 468 Et H s-Bu Me Cl SO₂Me 469 Me H s-Bu Me CH₂SO₂Me SO₂Me 470 Me H s-Bu Me CH₂OEt SO₂Me 471 Me H s-Bu Cl CH₂OMe SO₂Me 472 Me H s-Bu Me CH₂CH₂OMe SO₂Me 473 Me H s-Bu Me CH₂OCH₂CH₂OMe SO₂Me 474 Me H s-Bu Me OCH₂CH₂OEt SO₂Me 475 Me H s-Bu Me OCH₂CH₂Cl SO₂Me 476 Me H s-Bu Me OCH₂CF₃ SO₂Me 477 Me H s-Bu Me CH₂OCH₂OMe SO₂Me 478 Me H s-Bu Me OCH₂CH₂SMe SO₂Me 479 Me H s-Bu Me CN SO₂Me 480 Me H s-Bu Me CH₂CN SO₂Me 481 Me H s-Bu Br CO₂Me SO₂Me 482 Et H s-Bu Cl CO₂Me SO₂Me 483 Me H s-Bu CN CO₂Me SO₂Me 484 Me H s-Bu Cl OCH₂CH₂OCF₃ SO₂Me 485 Et H s-Bu Cl OCH₂CH₂OCF₃ SO₂Me 486 Me H s-Bu Me OCH₂CH₂OCF₃ SO₂Me 487 Et H s-Bu Me OCH₂CH₂OCF₃ SO₂Me 488 Me H s-Bu CF₃ OCH₂CH₂OCF₃ SO₂Me 489 Et H s-Bu CF₃ OCH₂CH₂OCF₃ SO₂Me 490 Me H s-Bu Br OCH₂CH₂OCF₃ SO₂Me 491 Et H s-Bu Br OCH₂CH₂OCF₃ SO₂Me 492 Me H s-Bu SO₂Me OCH₂CH₂OCF₃ CF₃ 493 Et H s-Bu SO₂Me OCH₂CH₂OCF₃ CF₃ 494 Me H s-Bu Cl OCH₂CH₂OCHClF SO₂Me 495 Et H s-Bu Cl OCH₂CH₂OCHClF SO₂Me 496 Me H s-Bu Me OCH₂CH₂OCHClF SO₂Me 497 Et H s-Bu Me OCH₂CH₂OCHClF SO₂Me 498 Me H s-Bu CF₃ OCH₂CH₂OCHClF SO₂Me 499 Et H s-Bu CF₃ OCH₂CH₂OCHClF SO₂Me 500 Me H s-Bu Br OCH₂CH₂OCHClF SO₂Me 501 Et H s-Bu Br OCH₂CH₂OCHClF SO₂Me 502 Me H s-Bu SO₂Me OCH₂CH₂OCHClF CF₃ 503 Et H s-Bu SO₂Me OCH₂CH₂OCHClF CF₃ 504 Me H s-Bu Cl OCH₂CHFOCF₃ SO₂Me 505 Et H s-Bu Cl OCH₂CHFOCF₃ SO₂Me 506 Me H s-Bu Me OCH₂CHFOCF₃ SO₂Me 507 Me H s-Bu Cl OCH₂CHFOMe SO₂Me 508 Et H s-Bu Cl OCH₂CHFOMe SO₂Me 509 Me H s-Bu Me OCH₂CHFOMe SO₂Me 510 Et H s-Bu Me OCH₂CHFOMe SO₂Me 511 Me H s-Bu CF₃ OCH₂CHFOMe SO₂Me 512 Et H s-Bu CF₃ OCH₂CHFOMe SO₂Me 513 Me H s-Bu Br OCH₂CHFOMe SO₂Me 514 Et H s-Bu Br OCH₂CHFOMe SO₂Me 515 Me H s-Bu SO₂Me OCH₂CHFOMe CF₃ 516 Et H s-Bu SO₂Me OCH₂CHFOMe CF₃ 517 Me H s-Bu Cl OCHFCH₂OCF₃ SO₂Me 518 Et H s-Bu Cl OCHFCH₂OCF₃ SO₂Me 519 Me H s-Bu Cl OCH₂CH₂OCF₂Cl SO₂Me 520 Et H s-Bu Cl OCH₂CH₂OCF₂Cl SO₂Me 521 Me H s-Bu Me OCH₂CH₂OCF₂Cl SO₂Me 522 Et H s-Bu Me OCH₂CH₂OCF₂Cl SO₂Me 523 Me H s-Bu CF₃ OCH₂CH₂OCF₂Cl SO₂Me 524 Et H s-Bu CF₃ OCH₂CH₂OCF₂Cl SO₂Me 525 Me H s-Bu Br OCH₂CH₂OCF₂Cl SO₂Me 526 Et H s-Bu Br OCH₂CH₂OCF₂Cl SO₂Me 527 Me H s-Bu SO₂Me OCH₂CH₂OCF₂Cl CF₃ 528 Et H s-Bu SO₂Me OCH₂CH₂OCF₂Cl CF₃ 529 Me H s-Bu Cl SCH₂CH₂OCH₃ SO₂Me 530 Et H s-Bu Cl SCH₂CH₂OCH₃ SO₂Me 531 Me H s-Bu Me SCH₂CH₂OCH₃ SO₂Me 532 Et H s-Bu Me SCH₂CH₂OCH₃ SO₂Me 533 Me H s-Bu CF₃ SCH₂CH₂OCH₃ SO₂Me 534 Et H s-Bu CF₃ SCH₂CH₂OCH₃ SO₂Me 535 Me H s-Bu Br SCH₂CH₂OCH₃ SO₂Me 536 Et H s-Bu Br SCH₂CH₂OCH₃ SO₂Me 537 Me H s-Bu SO₂Me SCH₂CH₂OCH₃ CF₃ 538 Et H s-Bu SO₂Me SCH₂CH₂OCH₃ CF₃ 539 Me H s-Bu Cl SCH₂CH₂OCF₃ SO₂Me 540 Et H s-Bu Cl SCH₂CH₂OCF₃ SO₂Me 541 Me H s-Bu Me SCH₂CH₂OCF₃ SO₂Me 542 Et H s-Bu Me SCH₂CH₂OCF₃ SO₂Me 543 Me H s-Bu CF₃ SCH₂CH₂OCF₃ SO₂Me 544 Et H s-Bu CF₃ SCH₂CH₂OCF₃ SO₂Me 545 Me H s-Bu Br SCH₂CH₂OCF₃ SO₂Me 546 Et H s-Bu Br SCH₂CH₂OCF₃ SO₂Me 547 Me H s-Bu SO₂Me SCH₂CH₂OCF₃ CF₃ 548 Et H s-Bu SO₂Me SCH₂CH₂OCF₃ CF₃ 549 Me H s-Bu Cl SCH₂CH₂SCH₃ SO₂Me 550 Et H s-Bu Cl SCH₂CH₂SCH₃ SO₂Me 551 Me H s-Bu Me SCH₂CH₂SCH₃ SO₂Me 552 Et H s-Bu Me SCH₂CH₂SCH₃ SO₂Me 553 Me H s-Bu CF₃ SCH₂CH₂SCH₃ SO₂Me 554 Et H s-Bu CF₃ SCH₂CH₂SCH₃ SO₂Me 555 Me H s-Bu Br SCH₂CH₂SCH₃ SO₂Me 556 Et H s-Bu Br SCH₂CH₂SCH₃ SO₂Me 557 Me H s-Bu SO₂Me SCH₂CH₂SCH₃ CF₃ 558 Et H s-Bu SO₂Me SCH₂CH₂SCH₃ CF₃ 559 Me H s-Bu Cl SCH₂CH₂SCF₃ SO₂Me 560 Et H s-Bu Cl SCH₂CH₂SCF₃ SO₂Me 561 Me H s-Bu Me SCH₂CH₂SCF₃ SO₂Me 562 Et H s-Bu Me SCH₂CH₂SCF₃ SO₂Me 563 Me H s-Bu CF₃ SCH₂CH₂SCF₃ SO₂Me 564 Et H s-Bu CF₃ SCH₂CH₂SCF₃ SO₂Me 565 Me H s-Bu Br SCH₂CH₂SCF₃ SO₂Me 566 Et H s-Bu Br SCH₂CH₂SCF₃ SO₂Me 567 Me H s-Bu SO₂Me SCH₂CH₂SCF₃ CF₃ 568 Et H s-Bu SO₂Me SCH₂CH₂SCF₃ CF₃ 569 Me H s-Bu Cl OCH₂CH(CH₃)OCH₃ SO₂Me 570 Et H s-Bu Cl OCH₂CH(CH₃)OCH₃ SO₂Me 571 Me H s-Bu Me OCH₂CH(CH₃)OCH₃ SO₂Me 572 Et H s-Bu Me OCH₂CH(CH₃)OCH₃ SO₂Me 573 Me H s-Bu CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 574 Et H s-Bu CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 575 Me H s-Bu Br OCH₂CH(CH₃)OCH₃ SO₂Me 576 Et H s-Bu Br OCH₂CH(CH₃)OCH₃ SO₂Me 577 Me H s-Bu SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 578 Et H s-Bu SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 579 Me H s-Bu Cl OCH₂CF₂OCH₃ SO₂Me 580 Et H s-Bu Cl OCH₂CF₂OCH₃ SO₂Me 581 Me H s-Bu Me OCH₂CF₂OCH₃ SO₂Me 582 Et H s-Bu Me OCH₂CF₂OCH₃ SO₂Me 583 Me H s-Bu CF₃ OCH₂CF₂OCH₃ SO₂Me 584 Et H s-Bu CF₃ OCH₂CF₂OCH₃ SO₂Me 585 Me H s-Bu Br OCH₂CF₂OCH₃ SO₂Me 586 Et H s-Bu Br OCH₂CF₂OCH₃ SO₂Me 587 Me H s-Bu SO₂Me OCH₂CF₂OCH₃ CF₃ 588 Et H s-Bu SO₂Me OCH₂CF₂OCH₃ CF₃ 589 Me H s-Bu Me OCH₂CH₂OCH₃ SO₂Me 590 Et H s-Bu Me OCH₂CH₂OCH₃ SO₂Me 591 Me H s-Bu Me OCH₂CH(OCH₃)₂ SO₂Me 592 Me H s-Bu Me CH₂N(Me)CH₂CN SO₂Me 593 Me H s-Bu Me (tetrahydrofuran-2-yl)methoxy SO₂Me 594 Me H s-Bu Cl SMe SO₂Me 595 Me H s-Bu Cl Cl SO₂Me 596 Me H s-Bu Cl OMe SO₂Me 597 Me H s-Bu Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 598 Me H s-Bu Cl OCH₂CH₂OMe SO₂Me 599 Me H s-Bu Me tetrahydrofuran-3-yloxy SO₂Me 600 Me H s-Bu Me OCH₂CH₂CH₂OMe SO₂Me 601 Me H s-Bu Me OCH₂CH₂OMe SO₂Me 602 Me H s-Bu OCHF₂ OCH₂CH₂OMe SO₂Me 603 Et H s-Bu Cl 2-(1,3-dioxolan-2-yl)ethoxy SO₂Me 604 Me H s-Bu Me propargyloxy SO₂Me 605 Me H s-Bu Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 606 Me H s-Bu Cl SO₂Me SO₂Me 607 Me H s-Bu Me (CH₂)₆Me SO₂Me 608 Me H s-Bu Me CH₂CH₂CH₂OMe SO₂Me 609 Et H s-Bu Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 610 Me H s-Bu Me CH₂N[C(O)SEt]CH₂CH₂CN SO₂Me 611 Me H s-Bu Me CH═CHCN SO₂Me 612 Me H s-Bu Me CH₂CH₂CN SO₂Me 613 Me H s-Bu Me CH₂SCN SO₂Me 614 Me H s-Bu Me CH₂C(S)NH₂ SO₂Me 615 Me H s-Bu Me OCH₂CH₂OMe SO₂Me 616 Et H s-Bu Me OCH₂CH₂OMe SO₂Me 617 Me H s-Bu Me OCH(CH₃)CH₂OMe SO₂Me 618 Et H s-Bu Me OCH₂CH(Et)OMe SO₂Me 619 Me H s-Bu Me (1,3-dioxolan-2-yl)methyl SO₂Me 620 Me H s-Bu Me CH₂O(i-Pr) SO₂Me 621 Me H s-Bu OCHF₂ CH₂OMe SO₂Me 622 Me H s-Bu CHF₂ CH₂OMe SO₂Me 623 Et H t-Bu Me CO₂(i-Pr) SO₂Me 624 Me H t-Bu Cl CO₂Et SO₂Me 625 Et H t-Bu Me CO₂Me CF₃ 626 Et H t-Bu Me OCH₂CH₂OMe SO₂Me 627 Et H t-Bu SO₂Me CO₂Me CN 628 Me H t-Bu Me C(O)SMe SO₂Me 629 Me H t-Bu Me C(O)SEt SO₂Me 630 Me H t-Bu Me 2-(2-oxolanyl)ethoxy SO₂Me 631 Me H t-Bu Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 632 Et H t-Bu Me CH₂OMe SO₂Me 633 Et H t-Bu Me 2-oxolanylmethoxymethyl SO₂Me 634 Me H t-Bu Cl CO₂Me SO₂Me 635 Et H t-Bu Cl CO₂Me SO₂Et 636 Me H t-Bu Cl C(O)SMe SO₂Me 637 Me H t-Bu Cl C(O)SEt SO₂Me 638 Me H t-Bu Me OMe SO₂Me 639 Me H t-Bu Me OEt SO₂Me 640 Me H t-Bu Me O(i-Pr) SO₂Me 641 Me H t-Bu Me OCHF₂ SO₂Me 642 Me H t-Bu Me (4,5-dihydroisoxazol-3-yl SO₂Me 643 Me H t-Bu Me O(n-Pr) SO₂Et 644 Me H t-Bu Cl CH₂OMe SO₂Me 645 Me H t-Bu Me OCO₂Me SO₂Me 646 Me H t-Bu Me OC(O)SMe SO₂Me 647 Me H t-Bu Me OC(O)SEt SO₂Me 648 Me H t-Bu Me OCH₂CH₂OMe SO₂Me 649 Et H t-Bu Me OEt SO₂Me 650 Et H t-Bu Cl CO₂Et SO₂Me 651 Et H t-Bu Cl CO₂(n-Pr) SO₂Me 652 Et H t-Bu Me CO₂Et SO₂Me 653 Me H t-Bu Me CH₂CO₂Et SO₂Me 654 Me H t-Bu Me OCH₂CO₂Et SO₂Me 655 Me H t-Bu Me O(n-Pr) SO₂Me 656 Et H t-Bu SO₂Me H CF₃ 657 Me H t-Bu Me CH₂OCH₂CF₃ SO₂Me 658 Me H t-Bu Cl CH₂OCH₂CF₃ SO₂Me 659 Et H t-Bu Me Cl SO₂Me 660 Me H t-Bu Me CH₂SO₂Me SO₂Me 661 Me H t-Bu Me CH₂OEt SO₂Me 662 Me H t-Bu Cl CH₂OMe SO₂Me 663 Me H t-Bu Me CH₂CH₂OMe SO₂Me 664 Me H t-Bu Me CH₂OCH₂CH₂OMe SO₂Me 665 Me H t-Bu Me OCH₂CH₂OEt SO₂Me 666 Me H t-Bu Me OCH₂CH₂Cl SO₂Me 667 Me H t-Bu Me OCH₂CF₃ SO₂Me 668 Me H t-Bu Me CH₂OCH₂OMe SO₂Me 669 Me H t-Bu Me OCH₂CH₂SMe SO₂Me 670 Me H t-Bu Me CN SO₂Me 671 Me H t-Bu Me CH₂CN SO₂Me 672 Me H t-Bu Br CO₂Me SO₂Me 673 Et H t-Bu Cl CO₂Me SO₂Me 674 Me H t-Bu Br CO₂Me SO₂Me 675 Me H t-Bu Cl OCH₂CH₂OCF₃ SO₂Me 676 Et H t-Bu Cl OCH₂CH₂OCF₃ SO₂Me 677 Me H t-Bu Me OCH₂CH₂OCF₃ SO₂Me 678 Et H t-Bu Me OCH₂CH₂OCF₃ SO₂Me 679 Me H t-Bu CF₃ OCH₂CH₂OCF₃ SO₂Me 680 Et H t-Bu CF₃ OCH₂CH₂OCF₃ SO₂Me 681 Me H t-Bu Br OCH₂CH₂OCF₃ SO₂Me 682 Et H t-Bu Br OCH₂CH₂OCF₃ SO₂Me 683 Me H t-Bu SO₂Me OCH₂CH₂OCF₃ CF₃ 684 Et H t-Bu SO₂Me OCH₂CH₂OCF₃ CF₃ 685 Me H t-Bu Cl OCH₂CH₂OCHClF SO₂Me 686 Et H t-Bu Cl OCH₂CH₂OCHClF SO₂Me 687 Me H t-Bu Me OCH₂CH₂OCHClF SO₂Me 688 Et H t-Bu Me OCH₂CH₂OCHClF SO₂Me 689 Me H t-Bu CF₃ OCH₂CH₂OCHClF SO₂Me 690 Et H t-Bu CF₃ OCH₂CH₂OCHClF SO₂Me 691 Me H t-Bu Br OCH₂CH₂OCHClF SO₂Me 692 Et H t-Bu Br OCH₂CH₂OCHClF SO₂Me 693 Me H t-Bu SO₂Me OCH₂CH₂OCHClF CF₃ 694 Et H t-Bu SO₂Me OCH₂CH₂OCHClF CF₃ 695 Me H t-Bu Cl OCH₂CHFOCF₃ SO₂Me 696 Et H t-Bu Cl OCH₂CHFOCF₃ SO₂Me 697 Me H t-Bu Me OCH₂CHFOCF₃ SO₂Me 698 Me H t-Bu Cl OCH₂CHFOMe SO₂Me 699 Et H t-Bu Cl OCH₂CHFOMe SO₂Me 700 Me H t-Bu Me OCH₂CHFOMe SO₂Me 701 Et H t-Bu Me OCH₂CHFOMe SO₂Me 702 Me H t-Bu CF₃ OCH₂CHFOMe SO₂Me 703 Et H t-Bu CF₃ OCH₂CHFOMe SO₂Me 704 Me H t-Bu Br OCH₂CHFOMe SO₂Me 705 Et H t-Bu Br OCH₂CHFOMe SO₂Me 706 Me H t-Bu SO₂Me OCH₂CHFOMe CF₃ 707 Et H t-Bu SO₂Me OCH₂CHFOMe CF₃ 708 Me H t-Bu Cl OCHFCH₂OCF₃ SO₂Me 709 Et H t-Bu Cl OCHFCH₂OCF₃ SO₂Me 710 Me H t-Bu Cl OCH₂CH₂OCF₂Cl SO₂Me 711 Et H t-Bu Cl OCH₂CH₂OCF₂Cl SO₂Me 712 Me H t-Bu Me OCH₂CH₂OCF₂Cl SO₂Me 713 Et H t-Bu Me OCH₂CH₂OCF₂Cl SO₂Me 714 Me H t-Bu CF₃ OCH₂CH₂OCF₂Cl SO₂Me 715 Et H t-Bu CF₃ OCH₂CH₂OCF₂Cl SO₂Me 716 Me H t-Bu Br OCH₂CH₂OCF₂Cl SO₂Me 717 Et H t-Bu Br OCH₂CH₂OCF₂Cl SO₂Me 718 Me H t-Bu SO₂Me OCH₂CH₂OCF₂Cl CF₃ 719 Et H t-Bu SO₂Me OCH₂CH₂OCF₂Cl CF₃ 720 Me H t-Bu Cl SCH₂CH₂OCH₃ SO₂Me 721 Et H t-Bu Cl SCH₂CH₂OCH₃ SO₂Me 722 Me H t-Bu Me SCH₂CH₂OCH₃ SO₂Me 723 Et H t-Bu Me SCH₂CH₂OCH₃ SO₂Me 724 Me H t-Bu CF₃ SCH₂CH₂OCH₃ SO₂Me 725 Et H t-Bu CF₃ SCH₂CH₂OCH₃ SO₂Me 726 Me H t-Bu Br SCH₂CH₂OCH₃ SO₂Me 727 Et H t-Bu Br SCH₂CH₂OCH₃ SO₂Me 728 Me H t-Bu SO₂Me SCH₂CH₂OCH₃ CF₃ 729 Et H t-Bu SO₂Me SCH₂CH₂OCH₃ CF₃ 730 Me H t-Bu Cl SCH₂CH₂OCF₃ SO₂Me 731 Et H t-Bu Cl SCH₂CH₂OCF₃ SO₂Me 732 Me H t-Bu Me SCH₂CH₂OCF₃ SO₂Me 733 Et H t-Bu Me SCH₂CH₂OCF₃ SO₂Me 734 Me H t-Bu CF₃ SCH₂CH₂OCF₃ SO₂Me 735 Et H t-Bu CF₃ SCH₂CH₂OCF₃ SO₂Me 736 Me H t-Bu Br SCH₂CH₂OCF₃ SO₂Me 737 Et H t-Bu Br SCH₂CH₂OCF₃ SO₂Me 738 Me H t-Bu SO₂Me SCH₂CH₂OCF₃ CF₃ 739 Et H t-Bu SO₂Me SCH₂CH₂OCF₃ CF₃ 740 Me H t-Bu Cl SCH₂CH₂SCH₃ SO₂Me 741 Et H t-Bu Cl SCH₂CH₂SCH₃ SO₂Me 742 Me H t-Bu Me SCH₂CH₂SCH₃ SO₂Me 743 Et H t-Bu Me SCH₂CH₂SCH₃ SO₂Me 744 Me H t-Bu CF₃ SCH₂CH₂SCH₃ SO₂Me 745 Et H t-Bu CF₃ SCH₂CH₂SCH₃ SO₂Me 746 Me H t-Bu Br SCH₂CH₂SCH₃ SO₂Me 747 Et H t-Bu Br SCH₂CH₂SCH₃ SO₂Me 748 Me H t-Bu SO₂Me SCH₂CH₂SCH₃ CF₃ 749 Et H t-Bu SO₂Me SCH₂CH₂SCH₃ CF₃ 750 Me H t-Bu Cl SCH₂CH₂SCF₃ SO₂Me 751 Et H t-Bu Cl SCH₂CH₂SCF₃ SO₂Me 752 Me H t-Bu Me SCH₂CH₂SCF₃ SO₂Me 753 Et H t-Bu Me SCH₂CH₂SCF₃ SO₂Me 754 Me H t-Bu CF₃ SCH₂CH₂SCF₃ SO₂Me 755 Et H t-Bu CF₃ SCH₂CH₂SCF₃ SO₂Me 756 Me H t-Bu Br SCH₂CH₂SCF₃ SO₂Me 757 Et H t-Bu Br SCH₂CH₂SCF₃ SO₂Me 758 Me H t-Bu SO₂Me SCH₂CH₂SCF₃ CF₃ 759 Et H t-Bu SO₂Me SCH₂CH₂SCF₃ CF₃ 760 Me H t-Bu Cl OCH₂CH(CH₃)OCH₃ SO₂Me 761 Et H t-Bu Cl OCH₂CH(CH₃)OCH₃ SO₂Me 762 Me H t-Bu Me OCH₂CH(CH₃)OCH₃ SO₂Me 763 Et H t-Bu Me OCH₂CH(CH₃)OCH₃ SO₂Me 764 Me H t-Bu CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 765 Et H t-Bu CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 766 Me H t-Bu Br OCH₂CH(CH₃)OCH₃ SO₂Me 767 Et H t-Bu Br OCH₂CH(CH₃)OCH₃ SO₂Me 768 Me H t-Bu SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 769 Et H t-Bu SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 770 Me H t-Bu Cl OCH₂CF₂OCH₃ SO₂Me 771 Et H t-Bu Cl OCH₂CF₂OCH₃ SO₂Me 772 Me H t-Bu Me OCH₂CF₂OCH₃ SO₂Me 773 Et H t-Bu Me OCH₂CF₂OCH₃ SO₂Me 774 Me H t-Bu CF₃ OCH₂CF₂OCH₃ SO₂Me 775 Et H t-Bu CF₃ OCH₂CF₂OCH₃ SO₂Me 776 Me H t-Bu Br OCH₂CF₂OCH₃ SO₂Me 777 Et H t-Bu Br OCH₂CF₂OCH₃ SO₂Me 778 Me H t-Bu SO₂Me OCH₂CF₂OCH₃ CF₃ 779 Et H t-Bu SO₂Me OCH₂CF₂OCH₃ CF₃ 780 Et H t-Bu CN OCH₂CF₂OCH₃ SO₂Me 781 Et H t-Bu Me OCH₂CF₂OCH₃ SO₂Me 782 Me H t-Bu Me OCH₂CH(OCH₃)₂ SO₂Me 783 Me H t-Bu Me CH₂N(Me)CH₂CN SO₂Me 784 Me H t-Bu Me (tetrahydrofuran-2-yl)methoxy SO₂Me 785 Me H t-Bu Cl SMe SO₂Me 786 Me H t-Bu Cl Cl SO₂Me 787 Me H t-Bu Cl OMe SO₂Me 788 Me H t-Bu Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 789 Me H t-Bu Cl OCH₂CH₂OMe SO₂Me 790 Me H t-Bu Me tetrahydrofuran-3-yloxy SO₂Me 791 Me H t-Bu Me OCH₂CH₂CH₂OMe SO₂Me 792 Me H t-Bu Me OCH₂CH₂OMe SO₂Me 793 Et H t-Bu Cl (1,3-dioxolan-2-yl)ethoxy SO₂Me 794 Me H t-Bu Me propargyloxy SO₂Me 795 Me H t-Bu Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 796 Me H t-Bu Cl SO₂Me SO₂Me 797 Me H t-Bu Me (CH₂)₆Me SO₂Me 798 Me H t-Bu Me CH₂CH₂CH₂OMe SO₂Me 799 Et H t-Bu Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 800 Me H t-Bu Me CH₂N[C(O)SEt]CH₂CN SO₂Me 801 Me H t-Bu Me CH═CHCN SO₂Me 802 Me H t-Bu Me CH₂CH₂CN SO₂Me 803 Me H t-Bu Me CH₂SCN SO₂Me 804 Me H t-Bu Me CH₂C(S)NH₂ SO₂Me 805 Me H t-Bu Me OCH₂CH₂OMe SO₂Me 806 Et H t-Bu Me OCH₂CH₂OMe SO₂Me 807 Me H t-Bu Me OCH(CH₃)CH₂OMe SO₂Me 808 Et H t-Bu Me OCH₂CH(Et)OMe SO₂Me 809 Me H t-Bu Me (1,3-dioxolan-2-yl)methyl SO₂Me 810 Me H t-Bu Me CH₂O(i-Pr) SO₂Me 811 Me Me t-Bu Me CO₂Me SO₂Me 812 Et Me t-Bu Me CO₂Me SO₂Me 813 Et Me t-Bu Me CO₂(i-Pr) SO₂Me 814 Me Me t-Bu Cl CO₂Et SO₂Me 815 Et Me t-Bu Me CO₂Me CF₃ 816 Et Me t-Bu Me OCH₂CH₂OMe SO₂Me 817 Et Me t-Bu SO₂Me CO₂Me CN 818 Me Me t-Bu Me C(O)SMe SO₂Me 819 Me Me t-Bu Me C(O)SEt SO₂Me 820 Me Me t-Bu Me 2-(2-oxolanyl)ethoxy SO₂Me 821 Me Me t-Bu Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 822 Et Me t-Bu Me CH₂OMe SO₂Me 823 Et Me t-Bu Me 2-oxolanylmethoxymethyl SO₂Me 824 Me Me t-Bu Cl CO₂Me SO₂Me 825 Et Me t-Bu Cl CO₂Me SO₂Et 826 Me Me t-Bu Cl C(O)SMe SO₂Me 827 Me Me t-Bu Cl C(O)SEt SO₂Me 828 Me Me t-Bu Me OMe SO₂Me 829 Me Me t-Bu Me OEt SO₂Me 830 Me Me t-Bu Me O(i-Pr) SO₂Me 831 Me Me t-Bu Me OCHF₂ SO₂Me 832 Me Me t-Bu Me (4,5-dihydroisoxazol-3-yl) SO₂Me 833 Me Me t-Bu Me O(n-Pr) SO₂Et 834 Me Me t-Bu Cl CH₂OMe SO₂Me 835 Me Me t-Bu Me OCO₂Me SO₂Me 836 Me Me t-Bu Me OC(O)SMe SO₂Me 837 Me Me t-Bu Me OC(O)SEt SO₂Me 838 Me Me t-Bu Me OCH₂CH₂OMe SO₂Me 839 Et Me t-Bu Me OEt SO₂Me 840 Et Me t-Bu Cl CO₂Et SO₂Me 841 Et Me t-Bu Cl CO₂(n-Pr) SO₂Me 842 Et Me t-Bu Me CO₂Et SO₂Me 843 Me Me t-Bu Me CH₂CO₂Me SO₂Me 844 Me Me t-Bu Me OCH₂CO₂Et SO₂Me 845 Me Me t-Bu Me O(n-Pr) SO₂Me 846 Et Me t-Bu SO₂Me H CF₃ 847 Me Me t-Bu Me CH₂OCH₂CF₃ SO₂Me 848 Me Me t-Bu Cl CH₂OCH₂CF₃ SO₂Me 849 Et Me t-Bu Me Cl SO₂Me 850 Me Me t-Bu Me CH₂SO₂Me SO₂Me 851 Me Me t-Bu Me CH₂OEt SO₂Me 852 Me Me t-Bu Cl CH₂OMe SO₂Me 853 Me Me t-Bu Me CH₂CH₂OMe SO₂Me 854 Me Me t-Bu Me CH₂OCH₂CH₂OMe SO₂Me 855 Me Me t-Bu Me OCH₂CH₂OEt SO₂Me 856 Me Me t-Bu Me OCH₂CH₂Cl SO₂Me 857 Me Me t-Bu Me OCH₂CF₃ SO₂Me 858 Me Me t-Bu Me CH₂OCH₂OMe SO₂Me 859 Me Me t-Bu Me OCH₂CH₂SMe SO₂Me 860 Me Me t-Bu Me CN SO₂Me 861 Me Me t-Bu Me CH₂CN SO₂Me 862 Me Me t-Bu Br CO₂Me SO₂Me 863 Et Me t-Bu Cl CO₂Me SO₂Me 864 Me Me t-Bu Br CO₂Me SO₂Me 865 Me Me t-Bu Cl OCH₂CH₂OCF₃ SO₂Me 866 Et Me t-Bu Cl OCH₂CH₂OCF₃ SO₂Me 867 Me Me t-Bu Me OCH₂CH₂OCF₃ SO₂Me 868 Et Me t-Bu Me OCH₂CH₂OCF₃ SO₂Me 869 Me Me t-Bu CF₃ OCH₂CH₂OCF₃ SO₂Me 870 Et Me t-Bu CF₃ OCH₂CH₂OCF₃ SO₂Me 871 Me Me t-Bu Br OCH₂CH₂OCF₃ SO₂Me 872 Et Me t-Bu Br OCH₂CH₂OCF₃ SO₂Me 873 Me Me t-Bu SO₂Me OCH₂CH₂OCF₃ CF₃ 874 Et Me t-Bu SO₂Me OCH₂CH₂OCF₃ CF₃ 875 Me Me t-Bu Cl OCH₂CH₂OCHClF SO₂Me 876 Et Me t-Bu Cl OCH₂CH₂OCHClF SO₂Me 877 Me Me t-Bu Me OCH₂CH₂OCHClF SO₂Me 878 Et Me t-Bu Me OCH₂CH₂OCHClF SO₂Me 879 Me Me t-Bu CF₃ OCH₂CH₂OCHClF SO₂Me 880 Et Me t-Bu CF₃ OCH₂CH₂OCHClF SO₂Me 881 Me Me t-Bu Br OCH₂CH₂OCHClF SO₂Me 882 Et Me t-Bu Br OCH₂CH₂OCHClF SO₂Me 883 Me Me t-Bu SO₂Me OCH₂CH₂OCHClF CF₃ 884 Et Me t-Bu SO₂Me OCH₂CH₂OCHClF CF₃ 885 Me Me t-Bu Cl OCH₂CHFOCF₃ SO₂Me 886 Et Me t-Bu Cl OCH₂CHFOCF₃ SO₂Me 887 Me Me t-Bu Me OCH₂CHFOCF₃ SO₂Me 888 Me Me t-Bu Cl OCH₂CHFOMe SO₂Me 889 Et Me t-Bu Cl OCH₂CHFOMe SO₂Me 890 Me Me t-Bu Me OCH₂CHFOMe SO₂Me 891 Et Me t-Bu Me OCH₂CHFOMe SO₂Me 892 Me Me t-Bu CF₃ OCH₂CHFOMe SO₂Me 893 Et Me t-Bu CF₃ OCH₂CHFOMe SO₂Me 894 Me Me t-Bu Br OCH₂CHFOMe SO₂Me 895 Et Me t-Bu Br OCH₂CHFOMe SO₂Me 896 Me Me t-Bu SO₂Me OCH₂CHFOMe CF₃ 897 Et Me t-Bu SO₂Me OCH₂CHFOMe CF₃ 898 Me Me t-Bu Cl OCHFCH₂OCF₃ SO₂Me 899 Et Me t-Bu Cl OCHFCH₂OCF₃ SO₂Me 900 Me Me t-Bu Cl OCH₂CH₂OCF₂Cl SO₂Me 901 Et Me t-Bu Cl OCH₂CH₂OCF₂Cl SO₂Me 902 Me Me t-Bu Me OCH₂CH₂OCF₂Cl SO₂Me 903 Et Me t-Bu Me OCH₂CH₂OCF₂Cl SO₂Me 904 Me Me t-Bu CF₃ OCH₂CH₂OCF₂Cl SO₂Me 905 Et Me t-Bu CF₃ OCH₂CH₂OCF₂Cl SO₂Me 906 Me Me t-Bu Br OCH₂CH₂OCF₂Cl SO₂Me 907 Et Me t-Bu Br OCH₂CH₂OCF₂Cl SO₂Me 908 Me Me t-Bu SO₂Me OCH₂CH₂OCF₂Cl CF₃ 909 Et Me t-Bu SO₂Me OCH₂CH₂OCF₂Cl CF₃ 910 Me Me t-Bu Cl SCH₂CH₂OCH₃ SO₂Me 911 Et Me t-Bu Cl SCH₂CH₂OCH₃ SO₂Me 912 Me Me t-Bu Me SCH₂CH₂OCH₃ SO₂Me 913 Et Me t-Bu Me SCH₂CH₂OCH₃ SO₂Me 914 Me Me t-Bu CF₃ SCH₂CH₂OCH₃ SO₂Me 915 Et Me t-Bu CF₃ SCH₂CH₂OCH₃ SO₂Me 916 Me Me t-Bu Br SCH₂CH₂OCH₃ SO₂Me 917 Et Me t-Bu Br SCH₂CH₂OCH₃ SO₂Me 918 Me Me t-Bu SO₂Me SCH₂CH₂OCH₃ CF₃ 919 Et Me t-Bu SO₂Me SCH₂CH₂OCH₃ CF₃ 920 Me Me t-Bu Cl SCH₂CH₂OCF₃ SO₂Me 921 Et Me t-Bu Cl SCH₂CH₂OCF₃ SO₂Me 922 Me Me t-Bu Me SCH₂CH₂OCF₃ SO₂Me 923 Et Me t-Bu Me SCH₂CH₂OCF₃ SO₂Me 924 Me Me t-Bu CF₃ SCH₂CH₂OCF₃ SO₂Me 925 Et Me t-Bu CF₃ SCH₂CH₂OCF₃ SO₂Me 926 Me Me t-Bu Br SCH₂CH₂OCF₃ SO₂Me 927 Et Me t-Bu Br SCH₂CH₂OCF₃ SO₂Me 928 Me Me t-Bu SO₂Me SCH₂CH₂OCF₃ CF₃ 929 Et Me t-Bu SO₂Me SCH₂CH₂OCF₃ CF₃ 930 Me Me t-Bu Cl SCH₂CH₂SCH₃ SO₂Me 931 Et Me t-Bu Cl SCH₂CH₂SCH₃ SO₂Me 932 Me Me t-Bu Me SCH₂CH₂SCH₃ SO₂Me 933 Et Me t-Bu Me SCH₂CH₂SCH₃ SO₂Me 934 Me Me t-Bu CF₃ SCH₂CH₂SCH₃ SO₂Me 935 Et Me t-Bu CF₃ SCH₂CH₂SCH₃ SO₂Me 936 Me Me t-Bu Br SCH₂CH₂SCH₃ SO₂Me 937 Et Me t-Bu Br SCH₂CH₂SCH₃ SO₂Me 938 Me Me t-Bu SO₂Me SCH₂CH₂SCH₃ CF₃ 939 Et Me t-Bu SO₂Me SCH₂CH₂SCH₃ CF₃ 940 Me Me t-Bu Cl SCH₂CH₂SCF₃ SO₂Me 941 Et Me t-Bu Cl SCH₂CH₂SCF₃ SO₂Me 942 Me Me t-Bu Me SCH₂CH₂SCF₃ SO₂Me 943 Et Me t-Bu Me SCH₂CH₂SCF₃ SO₂Me 944 Me Me t-Bu CF₃ SCH₂CH₂SCF₃ SO₂Me 945 Et Me t-Bu CF₃ SCH₂CH₂SCF₃ SO₂Me 946 Me Me t-Bu Br SCH₂CH₂SCF₃ SO₂Me 947 Et Me t-Bu Br SCH₂CH₂SCF₃ SO₂Me 948 Me Me t-Bu SO₂Me SCH₂CH₂SCF₃ CF₃ 949 Et Me t-Bu SO₂Me SCH₂CH₂SCF₃ CF₃ 950 Me Me t-Bu Cl OCH₂CH(CH₃)OCH₃ SO₂Me 951 Et Me t-Bu Cl OCH₂CH(CH₃)OCH₃ SO₂Me 952 Me Me t-Bu Me OCH₂CH(CH₃)OCH₃ SO₂Me 953 Et Me t-Bu Me OCH₂CH(CH₃)OCH₃ SO₂Me 954 Me Me t-Bu CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 955 Et Me t-Bu CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 956 Me Me t-Bu Br OCH₂CH(CH₃)OCH₃ SO₂Me 957 Et Me t-Bu Br OCH₂CH(CH₃)OCH₃ SO₂Me 958 Me Me t-Bu SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 959 Et Me t-Bu SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 960 Me Me t-Bu Cl OCH₃CF₂OCH₃ SO₂Me 961 Et Me t-Bu Cl OCH₃CF₂OCH₃ SO₂Me 962 Me Me t-Bu Me OCH₃CF₂OCH₃ SO₂Me 963 Et Me t-Bu Me OCH₃CF₂OCH₃ SO₂Me 964 Me Me t-Bu CF₃ OCH₃CF₂OCH₃ SO₂Me 965 Et Me t-Bu CF₃ OCH₃CF₂OCH₃ SO₂Me 966 Me Me t-Bu Br OCH₃CF₂OCH₃ SO₂Me 967 Et Me t-Bu Br OCH₃CF₂OCH₃ SO₂Me 968 Me Me t-Bu SO₂Me OCH₃CF₂OCH₃ CF₃ 969 Et Me t-Bu SO₂Me OCH₃CF₂OCH₃ CF₃ 970 Me Me t-Bu Me OCH₃CH₂OCH₃ SO₂Me 971 Et Me t-Bu Me OCH₃CH₂OCH₃ SO₂Me 972 Me Me t-Bu Me OCH₂CH(OCH₃)₂ SO₂Me 973 Me Me t-Bu Me CH₂N(Me)CH₂CN SO₂Me 974 Me Me t-Bu Me (tetrahydrofuran-2-yl)methoxy SO₂Me 975 Me Me t-Bu Cl SMe SO₂Me 976 Me Me t-Bu Cl Cl SO₂Me 977 Me Me t-Bu Cl OMe SO₂Me 978 Me Me t-Bu Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 979 Me Me t-Bu Cl OCH₂CH₂OMe SO₂Me 980 Me Me t-Bu Me Tetrahydrofuran-3-yloxy SO₂Me 981 Me Me t-Bu Me OCH₂CH₂CH₂OMe SO₂Me 982 Me Me t-Bu Me OCH₂CH₂OMe SO₂Me 983 Et Me t-Bu Cl (1,3-dioxolan-2-yl)ethoxy SO₂Me 984 Me Me t-Bu Me propargyloxy SO₂Me 985 Me Me t-Bu Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 986 Me Me t-Bu Cl SO₂Me SO₂Me 987 Me Me t-Bu Me (CH₂)₆Me SO₂Me 988 Me Me t-Bu Me CH₂CH₂CH₂OMe SO₂Me 989 Et Me t-Bu Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 990 Me Me t-Bu Me CH₂N[C(O)SEt]CH₂CN SO₂Me 991 Me Me t-Bu Me CH═CHCN SO₂Me 992 Me Me t-Bu Me CH₂CH₂CN SO₂Me 993 Me Me t-Bu Me CH₂SCN SO₂Me 994 Me Me t-Bu Me CH₂C(S)NH₂ SO₂Me 995 Me Me t-Bu Me OCH₂CH₂OMe SO₂Me 996 Et Me t-Bu Me OCH₂CH₂OMe SO₂Me 997 Me Me t-Bu Me OCH(CH₃)CH₂OMe SO₂Me 998 Et Me t-Bu Me OCH₂CH(Et)OMe SO₂Me 999 Me Me t-Bu Me (1,3-dioxolan-2-yl)methyl SO₂Me 1000 Me Me t-Bu Me CH₂O(i-Pr) SO₂Me 1001 Me H CH(Et)₂ Me CO₂Me SO₂Me 1002 Et H CH(Et)₂ Me CO₂Me SO₂Me 1003 Et H CH(Et)₂ Me CO₂(i-Pr) SO₂Me 1004 Me H CH(Et)₂ Cl CO₂Et SO₂Me 1005 Et H CH(Et)₂ Me CO₂Me CF₃ 1006 Et H CH(Et)₂ Me OCH₂CH₂OMe SO₂Me 1007 Et H CH(Et)₂ SO₂Me CO₂Me CN 1008 Me H CH(Et)₂ Me C(O)SMe SO₂Me 1009 Me H CH(Et)₂ Me C(O)SEt SO₂Me 1010 Me H CH(Et)₂ Me 2-(2-oxolanyl)ethoxy SO₂Me 1011 Me H CH(Et)₂ Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 1012 Et H CH(Et)₂ Me CH₂OMe SO₂Me 1013 Et H CH(Et)₂ Me 2-oxolanylmethoxymethyl SO₂Me 1014 Me H CH(Et)₂ Cl CO₂Me SO₂Me 1015 Et H CH(Et)₂ Cl CO₂Me SO₂Et 1016 Me H CH(Et)₂ Cl C(O)SMe SO₂Me 1017 Me H CH(Et)₂ Cl C(O)SEt SO₂Me 1018 Me H CH(Et)₂ Me OMe SO₂Me 1019 Me H CH(Et)₂ Me OEt SO₂Me 1020 Me H CH(Et)₂ Me O(i-Pr) SO₂Me 1021 Me H CH(Et)₂ Me OCHF₂ SO₂Me 1022 Me H CH(Et)₂ Me (4,5-dihydroisoxazol-3-yl) SO₂Me 1023 Me H CH(Et)₂ Me O(n-Pr) SO₂Et 1024 Me H CH(Et)₂ Cl CH₂OMe SO₂Me 1025 Me H CH(Et)₂ Me OCO₂Me SO₂Me 1026 Me H CH(Et)₂ Me OC(O)SMe SO₂Me 1027 Me H CH(Et)₂ Me OC(O)SEt SO₂Me 1028 Me H CH(Et)₂ Me OCH₂CH₂OMe SO₂Me 1029 Et H CH(Et)₂ Me OEt SO₂Me 1030 Et H CH(Et)₂ Cl CO₂Et SO₂Me 1031 Et H CH(Et)₂ Cl CO₂(n-Pr) SO₂Me 1032 Et H CH(Et)₂ Me CO₂Et SO₂Me 1033 Me H CH(Et)₂ Me CH₂CO₂Me SO₂Me 1034 Me H CH(Et)₂ Me OCH₂CO₂Et SO₂Me 1035 Me H CH(Et)₂ Me O(n-Pr) SO₂Me 1036 Et H CH(Et)₂ SO₂Me H CF₃ 1037 Me H CH(Et)₂ Me CH₂OCH₂CF₃ SO₂Me 1038 Me H CH(Et)₂ Cl CH₂OCH₂CF₃ SO₂Me 1039 Et H CH(Et)₂ Me Cl SO₂Me 1040 Me H CH(Et)₂ Me CH₂SO₂Me SO₂Me 1041 Me H CH(Et)₂ Me CH₂OEt SO₂Me 1042 Me H CH(Et)₂ Cl CH₂OMe SO₂Me 1043 Me H CH(Et)₂ Me CH₂CH₂OMe SO₂Me 1044 Me H CH(Et)₂ Me CH₂OCH₂CH₂OMe SO₂Me 1045 Me H CH(Et)₂ Me OCH₂CH₂OEt SO₂Me 1046 Me H CH(Et)₂ Me OCH₂CH₂Cl SO₂Me 1047 Me H CH(Et)₂ Me OCH₂CF₃ SO₂Me 1048 Me H CH(Et)₂ Me CH₂OCH₂OMe SO₂Me 1049 Me H CH(Et)₂ Me OCH₂CH₂SMe SO₂Me 1050 Me H CH(Et)₂ Me CN SO₂Me 1051 Me H CH(Et)₂ Me CH₂CN SO₂Me 1052 Me H CH(Et)₂ Br CO₂Me SO₂Me 1053 Et H CH(Et)₂ Cl CO₂Me SO₂Me 1054 Me H CH(Et)₂ Br CO₂Me SO₂Me 1055 Me H CH(Et)₂ Cl OCH₂CH₂OCF₃ SO₂Me 1056 Et H CH(Et)₂ Cl OCH₂CH₂OCF₃ SO₂Me 1057 Me H CH(Et)₂ Me OCH₂CH₂OCF₃ SO₂Me 1058 Et H CH(Et)₂ Me OCH₂CH₂OCF₃ SO₂Me 1059 Me H CH(Et)₂ CF₃ OCH₂CH₂OCF₃ SO₂Me 1060 Et H CH(Et)₂ CF₃ OCH₂CH₂OCF₃ SO₂Me 1061 Me H CH(Et)₂ Br OCH₂CH₂OCF₃ SO₂Me 1062 Et H CH(Et)₂ Br OCH₂CH₂OCF₃ SO₂Me 1063 Me H CH(Et)₂ SO₂Me OCH₂CH₂OCF₃ CF₃ 1064 Et H CH(Et)₂ SO₂Me OCH₂CH₂OCF₃ CF₃ 1065 Me H CH(Et)₂ Cl OCH₂CH₂OCHClF SO₂Me 1066 Et H CH(Et)₂ Cl OCH₂CH₂OCHClF SO₂Me 1067 Me H CH(Et)₂ Me OCH₂CH₂OCHClF SO₂Me 1068 Et H CH(Et)₂ Me OCH₂CH₂OCHClF SO₂Me 1069 Me H CH(Et)₂ CF₃ OCH₂CH₂OCHClF SO₂Me 1070 Et H CH(Et)₂ CF₃ OCH₂CH₂OCHClF SO₂Me 1071 Me H CH(Et)₂ Br OCH₂CH₂OCHClF SO₂Me 1072 Et H CH(Et)₂ Br OCH₂CH₂OCHClF SO₂Me 1073 Me H CH(Et)₂ SO₂Me OCH₂CH₂OCHClF CF₃ 1074 Et H CH(Et)₂ SO₂Me OCH₂CH₂OCHClF CF₃ 1075 Me H CH(Et)₂ Cl OCH₂CHFOCF₃ SO₂Me 1076 Et H CH(Et)₂ Cl OCH₂CHFOCF₃ SO₂Me 1077 Me H CH(Et)₂ Me OCH₂CHFOCF₃ SO₂Me 1078 Me H CH(Et)₂ Cl OCH₂CHFOMe SO₂Me 1079 Et H CH(Et)₂ Cl OCH₂CHFOMe SO₂Me 1080 Me H CH(Et)₂ Me OCH₂CHFOMe SO₂Me 1081 Et H CH(Et)₂ Me OCH₂CHFOMe SO₂Me 1082 Me H CH(Et)₂ CF₃ OCH₂CHFOMe SO₂Me 1083 Et H CH(Et)₂ CF₃ OCH₂CHFOMe SO₂Me 1084 Me H CH(Et)₂ Br OCH₂CHFOMe SO₂Me 1085 Et H CH(Et)₂ Br OCH₂CHFOMe SO₂Me 1086 Me H CH(Et)₂ SO₂Me OCH₂CHFOMe CF₃ 1087 Et H CH(Et)₂ SO₂Me OCH₂CHFOMe CF₃ 1088 Me H CH(Et)₂ Cl OCHFCH₂OCF₃ SO₂Me 1089 Et H CH(Et)₂ Cl OCHFCH₂OCF₃ SO₂Me 1090 Me H CH(Et)₂ Cl OCH₂CH₂OCF₂Cl SO₂Me 1091 Et H CH(Et)₂ Cl OCH₂CH₂OCF₂Cl SO₂Me 1092 Me H CH(Et)₂ Me OCH₂CH₂OCF₂Cl SO₂Me 1093 Et H CH(Et)₂ Me OCH₂CH₂OCF₂Cl SO₂Me 1094 Me H CH(Et)₂ CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1095 Et H CH(Et)₂ CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1096 Me H CH(Et)₂ Br OCH₂CH₂OCF₂Cl SO₂Me 1097 Et H CH(Et)₂ Br OCH₂CH₂OCF₂Cl SO₂Me 1098 Me H CH(Et)₂ SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1099 Et H CH(Et)₂ SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1100 Me H CH(Et)₂ Cl SCH₂CH₂OCH₃ SO₂Me 1101 Et H CH(Et)₂ Cl SCH₂CH₂OCH₃ SO₂Me 1102 Me H CH(Et)₂ Me SCH₂CH₂OCH₃ SO₂Me 1103 Et H CH(Et)₂ Me SCH₂CH₂OCH₃ SO₂Me 1104 Me H CH(Et)₂ CF₃ SCH₂CH₂OCH₃ SO₂Me 1105 Et H CH(Et)₂ CF₃ SCH₂CH₂OCH₃ SO₂Me 1106 Me H CH(Et)₂ Br SCH₂CH₂OCH₃ SO₂Me 1107 Et H CH(Et)₂ Br SCH₂CH₂OCH₃ SO₂Me 1108 Me H CH(Et)₂ SO₂Me SCH₂CH₂OCH₃ CF₃ 1109 Et H CH(Et)₂ SO₂Me SCH₂CH₂OCH₃ CF₃ 1110 Me H CH(Et)₂ Cl SCH₂CH₂OCF₃ SO₂Me 1111 Et H CH(Et)₂ Cl SCH₂CH₂OCF₃ SO₂Me 1112 Me H CH(Et)₂ Me SCH₂CH₂OCF₃ SO₂Me 1113 Et H CH(Et)₂ Me SCH₂CH₂OCF₃ SO₂Me 1114 Me H CH(Et)₂ CF₃ SCH₂CH₂OCF₃ SO₂Me 1115 Et H CH(Et)₂ CF₃ SCH₂CH₂OCF₃ SO₂Me 1116 Me H CH(Et)₂ Br SCH₂CH₂OCF₃ SO₂Me 1117 Et H CH(Et)₂ Br SCH₂CH₂OCF₃ SO₂Me 1118 Me H CH(Et)₂ SO₂Me SCH₂CH₂OCF₃ CF₃ 1119 Et H CH(Et)₂ SO₂Me SCH₂CH₂OCF₃ CF₃ 1120 Me H CH(Et)₂ Cl SCH₂CH₂SCH₃ SO₂Me 1121 Et H CH(Et)₂ Cl SCH₂CH₂SCH₃ SO₂Me 1122 Me H CH(Et)₂ Me SCH₂CH₂SCH₃ SO₂Me 1123 Et H CH(Et)₂ Me SCH₂CH₂SCH₃ SO₂Me 1124 Me H CH(Et)₂ CF₃ SCH₂CH₂SCH₃ SO₂Me 1125 Et H CH(Et)₂ CF₃ SCH₂CH₂SCH₃ SO₂Me 1126 Me H CH(Et)₂ Br SCH₂CH₂SCH₃ SO₂Me 1127 Et H CH(Et)₂ Br SCH₂CH₂SCH₃ SO₂Me 1128 Me H CH(Et)₂ SO₂Me SCH₂CH₂SCH₃ CF₃ 1129 Et H CH(Et)₂ SO₂Me SCH₂CH₂SCH₃ CF₃ 1130 Me H CH(Et)₂ Cl SCH₂CH₂SCF₃ SO₂Me 1131 Et H CH(Et)₂ Cl SCH₂CH₂SCF₃ SO₂Me 1132 Me H CH(Et)₂ Me SCH₂CH₂SCF₃ SO₂Me 1133 Et H CH(Et)₂ Me SCH₂CH₂SCF₃ SO₂Me 1134 Me H CH(Et)₂ CF₃ SCH₂CH₂SCF₃ SO₂Me 1135 Et H CH(Et)₂ CF₃ SCH₂CH₂SCF₃ SO₂Me 1136 Me H CH(Et)₂ Br SCH₂CH₂SCF₃ SO₂Me 1137 Et H CH(Et)₂ Br SCH₂CH₂SCF₃ SO₂Me 1138 Me H CH(Et)₂ SO₂Me SCH₂CH₂SCF₃ CF₃ 1139 Et H CH(Et)₂ SO₂Me SCH₂CH₂SCF₃ CF₃ 1140 Me H CH(Et)₂ Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1141 Et H CH(Et)₂ Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1142 Me H CH(Et)₂ Me OCH₂CH(CH₃)OCH₃ SO₂Me 1143 Et H CH(Et)₂ Me OCH₂CH(CH₃)OCH₃ SO₂Me 1144 Me H CH(Et)₂ CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1145 Et H CH(Et)₂ CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1146 Me H CH(Et)₂ Br OCH₂CH(CH₃)OCH₃ SO₂Me 1147 Et H CH(Et)₂ Br OCH₂CH(CH₃)OCH₃ SO₂Me 1148 Me H CH(Et)₂ SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1149 Et H CH(Et)₂ SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1150 Me H CH(Et)₂ Cl OCH₂CF₂OCH₃ SO₂Me 1151 Et H CH(Et)₂ Cl OCH₂CF₂OCH₃ SO₂Me 1152 Me H CH(Et)₂ Me OCH₂CF₂OCH₃ SO₂Me 1153 Et H CH(Et)₂ Me OCH₂CF₂OCH₃ SO₂Me 1154 Me H CH(Et)₂ CF₃ OCH₂CF₂OCH₃ SO₂Me 1155 Et H CH(Et)₂ CF₃ OCH₂CF₂OCH₃ SO₂Me 1156 Me H CH(Et)₂ Br OCH₂CF₂OCH₃ SO₂Me 1157 Et H CH(Et)₂ Br OCH₂CF₂OCH₃ SO₂Me 1158 Me H CH(Et)₂ SO₂Me OCH₂CF₂OCH₃ CF₃ 1159 Et H CH(Et)₂ SO₂Me OCH₂CF₂OCH₃ CF₃ 1160 Me H CH(Et)₂ CN OCH₂CH₂OCH₃ SO₂Me 1161 Et H CH(Et)₂ Me OCH₂CH₂OCH₃ SO₂Me 1162 Me H CH(Et)₂ Me OCH₂CH(OCH₃)₂ SO₂Me 1163 Me H CH(Et)₂ Me CH₂N(Me)CH₂CN SO₂Me 1164 Me H CH(Et)₂ Me (tetrahydrofuran-2-yl)methoxy SO₂Me 1165 Me H CH(Et)₂ Cl SMe SO₂Me 1166 Me H CH(Et)₂ Cl Cl SO₂Me 1167 Me H CH(Et)₂ Cl OMe SO₂Me 1168 Me H CH(Et)₂ Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 1169 Me H CH(Et)₂ Cl OCH₂CH₂OMe SO₂Me 1170 Me H CH(Et)₂ Me tetrahydrofuran-3-yloxy SO₂Me 1171 Me H CH(Et)₂ Me OCH₂CH₂CH₂OMe SO₂Me 1172 Me H CH(Et)₂ NO₂ OCH₂CH₂OMe SO₂Me 1173 Et H CH(Et)₂ Cl (1,3-dioxolan-2-yl)ethoxy SO₂Me 1174 Me H CH(Et)₂ Me propargyloxy SO₂Me 1175 Me H CH(Et)₂ Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 1176 Me H CH(Et)₂ Cl SO₂Me SO₂Me 1177 Me H CH(Et)₂ Me (CH₂)₆Me SO₂Me 1178 Me H CH(Et)₂ Me CH₂CH₂CH₂OMe SO₂Me 1179 Et H CH(Et)₂ Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 1180 Me H CH(Et)₂ Me CH₂N[C(O)SEt]CH₂CN SO₂Me 1181 Me H CH(Et)₂ Me CH═CHCN SO₂Me 1182 Me H CH(Et)₂ Me CH₂CH₂CN SO₂Me 1183 Me H CH(Et)₂ Me CH₂SCN SO₂Me 1184 Me H CH(Et)₂ Me CH₂C(S)NH₂ SO₂Me 1185 Me H CH(Et)₂ Me OCH₂CH₂OMe SO₂Me 1186 Et H CH(Et)₂ Me OCH₂CH₂OMe SO₂Me 1187 Me H CH(Et)₂ Me OCH(CH₃)CH₂OMe SO₂Me 1188 Et H CH(Et)₂ Me OCH₂CH(Et)OMe SO₂Me 1189 Me H CH(Et)₂ Me (1,3-dioxolan-2-yl)methyl SO₂Me 1190 Me H CH(Et)₂ Me CH₂O(i-Pr) SO₂Me 1191 i-Pr H Et Me CO₂Me SO₂Me 1192 t-Bu H Et Me CO₂Me SO₂Me 1193 t-Bu H Me Me CO₂(i-Pr) SO₂Me 1194 i-Pr H Me Cl CO₂Et SO₂Me 1195 t-Bu H Et Me CO₂Me CF₃ 1196 t-Bu H Et Me OCH₂CH₂OMe SO₂Me 1197 t-Bu H Me SO₂Me CO₂Me CN 1198 i-Pr H Me Me C(O)SMe SO₂Me 1199 i-Pr H Et Me C(O)SEt SO₂Me 1200 i-Pr H Me Me 2-(2-oxolanyl)ethoxy SO₂Me 1201 i-Pr H Et Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 1202 t-Bu H Et Me CH₂OMe SO₂Me 1203 t-Bu H Et Me 2-oxolanylmethoxymethyl SO₂Me 1204 i-Pr H Et Cl CO₂Me SO₂Me 1205 t-Bu H Et Cl CO₂Me SO₂Et 1206 i-Pr H Et Cl C(O)SMe SO₂Me 1207 i-Pr H Et Cl C(O)SEt SO₂Me 1208 i-Pr H Et Me OMe SO₂Me 1209 i-Pr H Et Me OEt SO₂Me 1210 i-Pr H Et Me O(i-Pr) SO₂Me 1211 i-Pr H Me Me OCHF₂ SO₂Me 1212 i-Pr H Me Me (4,5-dihydroisoxazol-3-yl) SO₂Me 1213 i-Pr H Et Me O(n-Pr) SO₂Et 1214 i-Pr H Et Cl CH₂OMe SO₂Me 1215 i-Pr H Et Me OCO₂Me SO₂Me 1216 i-Pr H Et Me OC(O)SMe SO₂Me 1217 i-Pr H Et Me OC(O)SEt SO₂Me 1218 i-Pr H Et Me OCH₂CH₂OMe SO₂Me 1219 t-Bu H Et Me OEt SO₂Me 1220 t-Bu H Me Cl CO₂Et SO₂Me 1221 t-Bu H Me Cl CO₂(n-Pr) SO₂Me 1222 t-Bu H Et Me CO₂Et SO₂Me 1223 i-Pr H Et Me CH₂CO₂Me SO₂Me 1224 i-Pr H Me Me OCH₂CO₂Et SO₂Me 1225 i-Pr H Me Me O(n-Pr) SO₂Me 1226 t-Bu H Et SO₂Me H CF₃ 1227 i-Pr H Me Me CH₂OCH₂CF₃ SO₂Me 1228 i-Pr H Et Cl CH₂OCH₂CF₃ SO₂Me 1229 t-Bu H Et Me Cl SO₂Me 1230 i-Pr H Et Me CH₂SO₂Me SO₂Me 1231 i-Pr H Et Me CH₂OEt SO₂Me 1232 i-Pr H Et CN CH₂OMe SO₂Me 1233 i-Pr H Et Me CH₂CH₂OMe SO₂Me 1234 i-Pr H Et Me CH₂OCH₂CH₂OMe SO₂Me 1235 i-Pr H Et Me OCH₂CH₂OEt SO₂Me 1236 i-Pr H Et Me OCH₂CH₂Cl SO₂Me 1237 i-Pr H Et Me OCH₂CF₃ SO₂Me 1238 i-Pr H Me Me CH₂OCH₂OMe SO₂Me 1239 i-Pr H Me Me OCH₂CH₂SMe SO₂Me 1240 i-Pr H Et Me CN SO₂Me 1241 i-Pr H Et Me CH₂CN SO₂Me 1242 i-Pr H Et Br CO₂Me SO₂Me 1243 t-Bu H Et Cl CO₂Me SO₂Me 1244 i-Pr H Et Br CO₂Me SO₂Me 1245 i-Pr H Et Cl OCH₂CH₂OCF₃ SO₂Me 1246 t-Bu H Et Cl OCH₂CH₂OCF₃ SO₂Me 1247 i-Pr H Me Me OCH₂CH₂OCF₃ SO₂Me 1248 t-Bu H Me Me OCH₂CH₂OCF₃ SO₂Me 1249 i-Pr H Et CF₃ OCH₂CH₂OCF₃ SO₂Me 1250 t-Bu H Et CF₃ OCH₂CH₂OCF₃ SO₂Me 1251 i-Pr H Me Br OCH₂CH₂OCF₃ SO₂Me 1252 t-Bu H Me Br OCH₂CH₂OCF₃ SO₂Me 1253 i-Pr H Et SO₂Me OCH₂CH₂OCF₃ CF₃ 1254 t-Bu H Et SO₂Me OCH₂CH₂OCF₃ CF₃ 1255 i-Pr H Et Cl OCH₂CH₂OCHClF SO₂Me 1256 t-Bu H Et Cl OCH₂CH₂OCHClF SO₂Me 1257 i-Pr H Et Me OCH₂CH₂OCHClF SO₂Me 1258 t-Bu H Et Me OCH₂CH₂OCHClF SO₂Me 1259 i-Pr H Et CF₃ OCH₂CH₂OCHClF SO₂Me 1260 t-Bu H Et CF₃ OCH₂CH₂OCHClF SO₂Me 1261 i-Pr H Et Br OCH₂CH₂OCHClF SO₂Me 1262 t-Bu H Et Br OCH₂CH₂OCHClF SO₂Me 1263 i-Pr H Et SO₂Me OCH₂CH₂OCHClF CF₃ 1264 t-Bu H Et SO₂Me OCH₂CH₂OCHClF CF₃ 1265 i-Pr H Me Cl OCH₂CHFOCF₃ SO₂Me 1266 t-Bu H Me Cl OCH₂CHFOCF₃ SO₂Me 1267 i-Pr H Et Me OCH₂CHFOCF₃ SO₂Me 1268 i-Pr H Et Cl OCH₂CHFOMe SO₂Me 1269 t-Bu H Et Cl OCH₂CHFOMe SO₂Me 1270 i-Pr H Et Me OCH₂CHFOMe SO₂Me 1271 t-Bu H Et Me OCH₂CHFOMe SO₂Me 1272 i-Pr H Et CF₃ OCH₂CHFOMe SO₂Me 1273 t-Bu H Et CF₃ OCH₂CHFOMe SO₂Me 1274 i-Pr H Me Br OCH₂CHFOMe SO₂Me 1275 t-Bu H Me Br OCH₂CHFOMe SO₂Me 1276 i-Pr H Et SO₂Me OCH₂CHFOMe CF₃ 1277 t-Bu H Et SO₂Me OCH₂CHFOMe CF₃ 1278 i-Pr H Me Cl OCHFCH₂OCF₃ SO₂Me 1279 t-Bu H Me Cl OCHFCH₂OCF₃ SO₂Me 1280 i-Pr H Et Cl OCH₂CH₂OCF₂Cl SO₂Me 1281 t-Bu H Me Cl OCH₂CH₂OCF₂Cl SO₂Me 1282 i-Pr H Et Me OCH₂CH₂OCF₂Cl SO₂Me 1283 t-Bu H Et Me OCH₂CH₂OCF₂Cl SO₂Me 1284 i-Pr H Et CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1285 t-Bu H Et CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1286 i-Pr H Et Br OCH₂CH₂OCF₂Cl SO₂Me 1287 t-Bu H Et Br OCH₂CH₂OCF₂Cl SO₂Me 1288 i-Pr H Et SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1289 t-Bu H Et SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1290 i-Pr H Et Cl SCH₂CH₂OCH₃ SO₂Me 1291 t-Bu H Et Cl SCH₂CH₂OCH₃ SO₂Me 1292 i-Pr H Me Me SCH₂CH₂OCH₃ SO₂Me 1293 t-Bu H Me Me SCH₂CH₂OCH₃ SO₂Me 1294 i-Pr H Et CF₃ SCH₂CH₂OCH₃ SO₂Me 1295 t-Bu H Et CF₃ SCH₂CH₂OCH₃ SO₂Me 1296 i-Pr H Et Br SCH₂CH₂OCH₃ SO₂Me 1297 t-Bu H Et Br SCH₂CH₂OCH₃ SO₂Me 1298 i-Pr H Et SO₂Me SCH₂CH₂OCH₃ CF₃ 1299 t-Bu H Et SO₂Me SCH₂CH₂OCH₃ CF₃ 1300 i-Pr H Et Cl SCH₂CH₂OCF₃ SO₂Me 1301 t-Bu H Me Cl SCH₂CH₂OCF₃ SO₂Me 1302 i-Pr H Me Me SCH₂CH₂OCF₃ SO₂Me 1303 t-Bu H Et Me SCH₂CH₂OCF₃ SO₂Me 1304 i-Pr H Et CF₃ SCH₂CH₂OCF₃ SO₂Me 1305 t-Bu H Me CF₃ SCH₂CH₂OCF₃ SO₂Me 1306 i-Pr H Me Br SCH₂CH₂OCF₃ SO₂Me 1307 t-Bu H Et Br SCH₂CH₂OCF₃ SO₂Me 1308 i-Pr H Me SO₂Me SCH₂CH₂OCF₃ CF₃ 1309 t-Bu H Et SO₂Me SCH₂CH₂OCF₃ CF₃ 1310 i-Pr H Et Cl SCH₂CH₂SCH₃ SO₂Me 1311 t-Bu H Et Cl SCH₂CH₂SCH₃ SO₂Me 1312 i-Pr H Et Me SCH₂CH₂SCH₃ SO₂Me 1313 t-Bu H Et Me SCH₂CH₂SCH₃ SO₂Me 1314 i-Pr H Et CF₃ SCH₂CH₂SCH₃ SO₂Me 1315 t-Bu H Et CF₃ SCH₂CH₂SCH₃ SO₂Me 1316 i-Pr H Et Br SCH₂CH₂SCH₃ SO₂Me 1317 t-Bu H Et Br SCH₂CH₂SCH₃ SO₂Me 1318 i-Pr H Et SO₂Me SCH₂CH₂SCH₃ CF₃ 1319 t-Bu H Et SO₂Me SCH₂CH₂SCH₃ CF₃ 1320 i-Pr H Me Cl SCH₂CH₂SCF₃ SO₂Me 1321 t-Bu H Me Cl SCH₂CH₂SCF₃ SO₂Me 1322 i-Pr H Et Me SCH₂CH₂SCF₃ SO₂Me 1323 t-Bu H Et Me SCH₂CH₂SCF₃ SO₂Me 1324 i-Pr H Et CF₃ SCH₂CH₂SCF₃ SO₂Me 1325 t-Bu H Et CF₃ SCH₂CH₂SCF₃ SO₂Me 1326 i-Pr H Et Br SCH₂CH₂SCF₃ SO₂Me 1327 t-Bu H Et Br SCH₂CH₂SCF₃ SO₂Me 1328 i-Pr H Me SO₂Me SCH₂CH₂SCF₃ CF₃ 1329 t-Bu H Me SO₂Me SCH₂CH₂SCF₃ CF₃ 1330 i-Pr H Et Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1331 t-Bu H Et Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1332 i-Pr H Me Me OCH₂CH(CH₃)OCH₃ SO₂Me 1333 t-Bu H Me Me OCH₂CH(CH₃)OCH₃ SO₂Me 1334 i-Pr H Et CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1335 t-Bu H Me CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1336 i-Pr H Et Br OCH₂CH(CH₃)OCH₃ SO₂Me 1337 t-Bu H Et Br OCH₂CH(CH₃)OCH₃ SO₂Me 1338 i-Pr H Et SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1339 t-Bu H Et SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1340 i-Pr H Et Cl OCH₂CF₂OCH₃ SO₂Me 1341 t-Bu H Et Cl OCH₂CF₂OCH₃ SO₂Me 1342 i-Pr H Et Me OCH₂CF₂OCH₃ SO₂Me 1343 t-Bu H Et Me OCH₂CF₂OCH₃ SO₂Me 1344 i-Pr H Et CF₃ OCH₂CF₂OCH₃ SO₂Me 1345 t-Bu H Et CF₃ OCH₂CF₂OCH₃ SO₂Me 1346 i-Pr H Me Br OCH₂CF₂OCH₃ SO₂Me 1347 t-Bu H Me Br OCH₂CF₂OCH₃ SO₂Me 1348 i-Pr H Et SO₂Me OCH₂CF₂OCH₃ CF₃ 1349 t-Bu H Et SO₂Me OCH₂CF₂OCH₃ CF₃ 1350 i-Pr H Et Me OCH₂CH₂OCH₃ SO₂Me 1351 t-Bu H Et Me OCH₂CH₂OCH₃ SO₂Me 1352 i-Pr H Et Me OCH₂CH(OCH₃)₂ SO₂Me 1353 i-Pr H Et Me CH₂NMeCH₂CN SO₂Me 1354 i-Pr H Et Me (tetrahydrofuran-2-yl)methoxy SO₂Me 1355 i-Pr H Me Cl SMe SO₂Me 1356 i-Pr H Me Cl Cl SO₂Me 1357 i-Pr H Et Cl OMe SO₂Me 1358 i-Pr H Et Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 1359 i-Pr H Me Cl OCH₂CH₂OMe SO₂Me 1360 i-Pr H Me Me Tetrahydrofuran-3-yloxy SO₂Me 1361 i-Pr H Et Me OCH₂CH₂CH₂OMe SO₂Me 1362 i-Pr H Me Me OCH₂CH₂OMe SO₂Me 1363 t-Bu H Et Cl (1,3-dioxolan-2-yl)ethoxy SO₂Me 1364 i-Pr H Et Me propargyloxy SO₂Me 1365 i-Pr H Et Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 1366 i-Pr H Et Cl SO₂Me SO₂Me 1367 i-Pr H Et Me (CH₂)₆Me SO₂Me 1368 i-Pr H Et Me CH₂CH₂CH₂OMe SO₂Me 1369 t-Bu H Et Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 1370 i-Pr H Et Me CH₂N[C(O)SEt]CH₂CN SO₂Me 1371 i-Pr H Et Me CH═CHCN SO₂Me 1372 i-Pr H Et Me CH₂CH₂CN SO₂Me 1373 i-Pr H Me Me CH₂SCN SO₂Me 1374 i-Pr H Me Me CH₂C(S)NH₂ SO₂Me 1375 i-Pr H Et Me OCH₂CH₂OMe SO₂Me 1376 t-Bu H Et Me OCH₂CH₂OMe SO₂Me 1377 i-Pr H Et Me OCH(CH₃)CH₂OMe SO₂Me 1378 t-Bu H Et Me OCH₂CH(Et)OMe SO₂Me 1379 i-Pr H Et Me (1,3-dioxolan-2-yl)methyl SO₂Me 1380 i-Pr H Et Me CH₂O(i-Pr) SO₂Me 1381 Et H i-Pr Me CO₂(i-Pr) SO₂Me 1382 Me H i-Pr Cl CO₂Et SO₂Me 1383 Et H i-Pr Me CO₂Me CF₃ 1384 Et H i-Pr SO₂Me CO₂Me CN 1385 Me H i-Pr Me C(O)SMe SO₂Me 1386 Me H i-Pr Me C(O)SEt SO₂Me 1387 Me H i-Pr Me 2-(2-oxolanyl)ethoxy SO₂Me 1388 Me H i-Pr Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 1389 Et H i-Pr Me CH₂OMe SO₂Me 1390 Et H i-Pr Me 2-oxolanylmethoxymethyl SO₂Me 1391 Me H i-Pr Cl CO₂Me SO₂Me 1392 Et H i-Pr Cl CO₂Me SO₂Et 1393 Me H i-Pr Cl C(O)SMe SO₂Me 1394 Me H i-Pr Cl C(O)SEt SO₂Me 1395 Me H i-Pr Me OMe SO₂Me 1396 Me H i-Pr Me OEt SO₂Me 1397 Me H i-Pr Me O(i-Pr) SO₂Me 1398 Me H i-Pr Me OCHF₂ SO₂Me 1399 Me H i-Pr Me (4.5-dihydroisoxazol-3-yl) SO₂Me 1400 Me H i-Pr Me O(n-Pr) SO₂Et 1401 Me H i-Pr Cl CH₂OMe SO₂Me 1402 Me H i-Pr Me OCO₂Me SO₂Me 1403 Me H i-Pr Me OC(O)SMe SO₂Me 1404 Me H i-Pr Me OC(O)SEt SO₂Me 1405 Et H i-Pr Me OEt SO₂Me 1406 Et H i-Pr Cl CO₂Et SO₂Me 1407 Et H i-Pr Cl CO₂(n-Pr) SO₂Me 1408 Et H i-Pr Me CO₂Et SO₂Me 1409 Me H i-Pr Me CH₂CO₂Me SO₂Me 1410 Me H i-Pr Me OCH₂CO₂Et SO₂Me 1411 Me H i-Pr Me O(n-Pr) SO₂Me 1412 Et H i-Pr SO₂Me H CF₃ 1413 Me H i-Pr Me CH₂OCH₂CF₃ SO₂Me 1414 Me H i-Pr Cl CH₂OCH₂CF₃ SO₂Me 1415 Et H i-Pr Me Cl SO₂Me 1416 Me H i-Pr Me CH₂SO₂Me SO₂Me 1417 Me H i-Pr Me CH₂OEt SO₂Me 1418 Me H i-Pr Cl CH₂OMe SO₂Me 1419 Me H i-Pr Me CH₂CH₂OMe SO₂Me 1420 Me H i-Pr Me CH₂OCH₂CH₂OMe SO₂Me 1421 Me H i-Pr Me OCH₂CH₂OEt SO₂Me 1422 Me H i-Pr Me OCH₂CH₂Cl SO₂Me 1423 Me H i-Pr Me OCH₂CF₃ SO₂Me 1424 Me H i-Pr Me CH₂OCH₂OMe SO₂Me 1425 Me H i-Pr Me OCH₂CH₂SMe SO₂Me 1426 Me H i-Pr Me CN SO₂Me 1427 Me H i-Pr Me CH₂CN SO₂Me 1428 Me H i-Pr Br CO₂Me SO₂Me 1429 Et H i-Pr Cl CO₂Me SO₂Me 1430 Me H i-Pr Br CO₂Me SO₂Me 1431 Me H i-Pr Cl OCH₂CH₂OCF₃ SO₂Me 1432 Et H i-Pr Cl OCH₂CH₂OCF₃ SO₂Me 1433 Me H i-Pr Me OCH₂CH₂OCF₃ SO₂Me 1434 Et H i-Pr Me OCH₂CH₂OCF₃ SO₂Me 1435 Me H i-Pr CF₃ OCH₂CH₂OCF₃ SO₂Me 1436 Et H i-Pr CF₃ OCH₂CH₂OCF₃ SO₂Me 1437 Me H i-Pr Br OCH₂CH₂OCF₃ SO₂Me 1438 Et H i-Pr Br OCH₂CH₂OCF₃ SO₂Me 1439 Me H i-Pr SO₂Me OCH₂CH₂OCF₃ CF₃ 1440 Et H i-Pr SO₂Me OCH₂CH₂OCF₃ CF₃ 1441 Me H i-Pr Cl OCH₂CH₂OCHClF SO₂Me 1442 Et H i-Pr Cl OCH₂CH₂OCHClF SO₂Me 1443 Me H i-Pr Me OCH₂CH₂OCHClF SO₂Me 1444 Et H i-Pr Me OCH₂CH₂OCHClF SO₂Me 1445 Me H i-Pr CF₃ OCH₂CH₂OCHClF SO₂Me 1446 Et H i-Pr CF₃ OCH₂CH₂OCHClF SO₂Me 1447 Me H i-Pr Br OCH₂CH₂OCHClF SO₂Me 1448 Et H i-Pr Br OCH₂CH₂OCHClF SO₂Me 1449 Me H i-Pr SO₂Me OCH₂CH₂OCHClF CF₃ 1450 Et H i-Pr SO₂Me OCH₂CH₂OCHClF CF₃ 1451 Me H i-Pr Cl OCH₂CHFOCF₃ SO₂Me 1452 Et H i-Pr Cl OCH₂CHFOCF₃ SO₂Me 1453 Me H i-Pr Me OCH₂CHFOCF₃ SO₂Me 1454 Me H i-Pr Cl OCH₂CHFOMe SO₂Me 1455 Et H i-Pr Cl OCH₂CHFOMe SO₂Me 1456 Me H i-Pr Me OCH₂CHFOMe SO₂Me 1457 Et H i-Pr Me OCH₂CHFOMe SO₂Me 1458 Me H i-Pr CF₃ OCH₂CHFOMe SO₂Me 1459 Et H i-Pr CF₃ OCH₂CHFOMe SO₂Me 1460 Me H i-Pr Br OCH₂CHFOMe SO₂Me 1461 Et H i-Pr Br OCH₂CHFOMe SO₂Me 1462 Me H i-Pr SO₂Me OCH₂CHFOMe CF₃ 1463 Et H i-Pr SO₂Me OCH₂CHFOMe CF₃ 1464 Me H i-Pr Cl OCHFCH₂OCF₃ SO₂Me 1465 Et H i-Pr Cl OCHFCH₂OCF₃ SO₂Me 1466 Me H i-Pr Cl OCH₂CH₂OCF₂Cl SO₂Me 1467 Et H i-Pr Cl OCH₂CH₂OCF₂Cl SO₂Me 1468 Me H i-Pr Me OCH₂CH₂OCF₂Cl SO₂Me 1469 Et H i-Pr Me OCH₂CH₂OCF₂Cl SO₂Me 1470 Me H i-Pr CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1471 Et H i-Pr CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1472 Me H i-Pr Br OCH₂CH₂OCF₂Cl SO₂Me 1473 Et H i-Pr Br OCH₂CH₂OCF₂Cl SO₂Me 1474 Me H i-Pr SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1475 Et H i-Pr SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1476 Me H i-Pr Cl SCH₂CH₂OCH₃ SO₂Me 1477 Et H i-Pr Cl SCH₂CH₂OCH₃ SO₂Me 1478 Me H i-Pr Me SCH₂CH₂OCH₃ SO₂Me 1479 Et H i-Pr Me SCH₂CH₂OCH₃ SO₂Me 1480 Me H i-Pr CF₃ SCH₂CH₂OCH₃ SO₂Me 1481 Et H i-Pr CF₃ SCH₂CH₂OCH₃ SO₂Me 1482 Me H i-Pr Br SCH₂CH₂OCH₃ SO₂Me 1483 Et H i-Pr Br SCH₂CH₂OCH₃ SO₂Me 1484 Me H i-Pr SO₂Me SCH₂CH₂OCH₃ CF₃ 1485 Et H i-Pr SO₂Me SCH₂CH₂OCH₃ CF₃ 1486 Me H i-Pr Cl SCH₂CH₂OCF₃ SO₂Me 1487 Et H i-Pr Cl SCH₂CH₂OCF₃ SO₂Me 1488 Me H i-Pr Me SCH₂CH₂OCF₃ SO₂Me 1489 Et H i-Pr Me SCH₂CH₂OCF₃ SO₂Me 1490 Me H i-Pr CF₃ SCH₂CH₂OCF₃ SO₂Me 1491 Et H i-Pr CF₃ SCH₂CH₂OCF₃ SO₂Me 1492 Me H i-Pr Br SCH₂CH₂OCF₃ SO₂Me 1493 Et H i-Pr Br SCH₂CH₂OCF₃ SO₂Et 1494 Me H i-Pr SO₂Me SCH₂CH₂OCF₃ CF₃ 1495 Et H i-Pr SO₂Me SCH₂CH₂OCF₃ CF₃ 1496 Me H i-Pr Cl SCH₂CH₂SCH₃ SO₂Me 1497 Et H i-Pr Cl SCH₂CH₂SCH₃ SO₂Me 1498 Me H i-Pr Me SCH₂CH₂SCH₃ SO₂Me 1499 Et H i-Pr Me SCH₂CH₂SCH₃ SO₂Me 1500 Me H i-Pr CF₃ SCH₂CH₂SCH₃ SO₂Me 1501 Et H i-Pr CF₃ SCH₂CH₂SCH₃ SO₂Me 1502 Me H i-Pr Br SCH₂CH₂SCH₃ SO₂Me 1503 Et H i-Pr Br SCH₂CH₂SCH₃ SO₂Me 1504 Me H i-Pr SO₂Me SCH₂CH₂SCH₃ CF₃ 1505 Et H i-Pr SO₂Me SCH₂CH₂SCH₃ CF₃ 1506 Me H i-Pr Cl SCH₂CH₂SCF₃ SO₂Me 1507 Et H i-Pr Cl SCH₂CH₂SCF₃ SO₂Me 1508 Me H i-Pr Me SCH₂CH₂SCF₃ SO₂Me 1509 Et H i-Pr Me SCH₂CH₂SCF₃ SO₂Me 1510 Me H i-Pr CF₃ SCH₂CH₂SCF₃ SO₂Me 1511 Et H i-Pr CF₃ SCH₂CH₂SCF₃ SO₂Me 1512 Me H i-Pr Br SCH₂CH₂SCF₃ SO₂Me 1513 Et H i-Pr Br SCH₂CH₂SCF₃ SO₂Me 1514 Me H i-Pr SO₂Me SCH₂CH₂SCF₃ CF₃ 1515 Et H i-Pr SO₂Me SCH₂CH₂SCF₃ CF₃ 1516 Me H i-Pr Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1517 Et H i-Pr Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1517 Me H i-Pr Me OCH₂CH(CH₃)OCH₃ SO₂Me 1518 Et H i-Pr Me OCH₂CH(CH₃)OCH₃ SO₂Me 1519 Me H i-Pr CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1520 Et H i-Pr CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1521 Me H i-Pr Br OCH₂CH(CH₃)OCH₃ SO₂Me 1522 Et H i-Pr Br OCH₂CH(CH₃)OCH₃ SO₂Me 1523 Me H i-Pr SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1524 Et H i-Pr SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1525 Me H i-Pr Cl OCH₂CF₂OCH₃ SO₂Me 1526 Et H i-Pr Cl OCH₂CF₂OCH₃ SO₂Me 1527 Me H i-Pr Me OCH₂CF₂OCH₃ SO₂Me 1528 Et H i-Pr Me OCH₂CF₂OCH₃ SO₂Me 1529 Me H i-Pr CF₃ OCH₂CF₂OCH₃ SO₂Me 1530 Et H i-Pr CF₃ OCH₂CF₂OCH₃ SO₂Me 1531 Me H i-Pr Br OCH₂CF₂OCH₃ SO₂Me 1532 Et H i-Pr Br OCH₂CF₂OCH₃ SO₂Me 1533 Me H i-Pr SO₂Me OCH₂CF₂OCH₃ CF₃ 1534 Et H i-Pr SO₂Me OCH₂CF₂OCH₃ CF₃ 1535 Me H i-Pr Me OCH₂CH₂OCH₃ SO₂Me 1536 Et H i-Pr Me OCH₂CH₂OCH₃ SO₂Me 1537 Me H i-Pr Me OCH₂CH(OCH₃)₂ SO₂Me 1538 Me H i-Pr Me CH₂N(Me)CH₂CN SO₂Me 1539 Me H i-Pr Me (tetrahydrofuran-2-yl)methoxy SO₂Me 1540 Me H i-Pr Cl SMe SO₂Me 1541 Me H i-Pr Cl Cl SO₂Me 1542 Me H i-Pr Cl OMe SO₂Me 1543 Me H i-Pr Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 1544 Me H i-Pr Cl OCH₂CH₂OMe SO₂Me 1545 Me H i-Pr Me tetrahydrofuran-3-yloxy SO₂Me 1546 Me H i-Pr Me OCH₂CH₂CH₂OMe SO₂Me 1547 Me H i-Pr Me OCH₂CH₂OMe SO₂Me 1548 Et H i-Pr Cl (1,3-dioxolan-2-yl)ethoxy SO₂Me 1549 Me H i-Pr Me propargyloxy SO₂Me 1550 Me H i-Pr Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 1551 Me H i-Pr Cl SO₂Me SO₂Me 1552 Me H i-Pr Me (CH₂)₆Me SO₂Me 1553 Me H i-Pr Me CH₂CH₂CH₂OMe SO₂Me 1554 Et H i-Pr Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 1555 Me H i-Pr Me CH₂N[C(O)SEt]CH₂CN SO₂Me 1556 Me H i-Pr Me CHCHCN SO₂Me 1557 Me H i-Pr Me CH₂CH₂CN SO₂Me 1558 Me H i-Pr Me CH₂SCN SO₂Me 1559 Me H i-Pr Me CH₂C(S)NH₂ SO₂Me 1560 Me H i-Pr Me OCH₂CH₂OMe SO₂Me 1561 Et H i-Pr Me OCH₂CH₂OMe SO₂Me 1562 Me H i-Pr Me OCH(CH₃)CH₂OMe SO₂Me 1563 Et H i-Pr Me OCH₂CH(Et)OMe SO₂Me 1564 Me H i-Pr Me (1,3-dioxolan-2-yl)methyl SO₂Me 1565 Me H i-Pr Me CH₂O(i-Pr) SO₂Me 1567 Me Me Et Me CO₂Me SO₂Me 1568 Et Me Et Me CO₂Me SO₂Me 1569 Me Me Me Me CO₂Me SO₂Me 1570 Et Me Me Me CO₂Me SO₂Me 1571 n-Pr Me Et Me CO₂Me SO₂Me 1572 c-Pr Me Et Me CO₂Me SO₂Me 1573 n-Pr Me Me Me CO₂Me SO₂Me 1574 c-Pr Me Me Me CO₂Me SO₂Me 1575 t-Bu Me Et Me CO₂Me SO₂Me 1576 t-Bu Me Me Me CO₂Me SO₂Me 1577 Et Me Et Me CO₂(i-Pr) SO₂Me 1578 Me Me Et Me CO₂Et SO₂Me 1579 Et Me Et Me CO₂Me NO₂ 1580 Et Me Et SO₂Me CO₂Me CF₃ 1581 Et Me Et Me OCH₂CH₂OMe SO₂Me 1582 Et Me Et Cl OCH₂CH₂OMe SO₂Me 1583 Et Me Et Me CO₂Me CN 1584 Me Me Et Me C(O)SMe SO₂Me 1585 Et Me Et Me C(O)SMe SO₂Me 1586 Me Me Me Me C(O)SEt SO₂Me 1587 Et Me Me Me C(O)SEt SO₂Me 1588 Me Me Et Me 2-(2-oxolanyl)ethoxy SO₂Me 1589 Me Me Et Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 1590 Et Me Et Me CH₂OMe SO₂Me 1591 Et Me Et Me 2-oxolanylmethoxymethyl SO₂Me 1592 Me Me Et Cl CO₂Me SO₂Et 1593 Et Me Et Cl CO₂Me SO₂Me 1594 Me Me Me Cl CO₂Me SO₂Me 1595 Et Me Me Br CO₂Me SO₂Me 1596 Me Me Et Cl C(O)SMe SO₂Me 1597 Et Me Et Cl C(O)SMe SO₂Me 1598 Me Me Et Cl C(O)SEt SO₂Me 1599 Et Me Et Cl C(O)SEt SO₂Me 1600 Me Me Et Me OMe SO₂Me 1601 Me Me Et Me OEt SO₂Me 1602 Me Me Et Me O(i-Pr) SO₂Me 1603 Me Me Et Me OCHF₂ SO₂Me 1604 Me Me Et Me (4,5-dihydroisoxazol-3-yl) SO₂Me 1605 Me Me Me Me (4,5-dihydroisoxazol-3-yl) SO₂Me 1606 Me Me Et Me O(n-Pr) SO₂Et 1607 Me Me Et Cl CH₂OMe SO₂Me 1608 Me Me Et Me OCO₂Me SO₂Me 1609 Et Me Et Me OCO₂Me SO₂Me 1610 Me Me Me Me OCO₂Me SO₂Me 1611 Et Me Me Me OCO₂Me SO₂Me 1612 Me Me Et Me OC(O)SMe SO₂Me 1613 Et Me Et Me OC(O)SMe SO₂Me 1614 Me Me Me Me OC(O)SMe SO₂Me 1615 Et Me Me Me OC(O)SMe SO₂Me 1616 Me Me Et Me OC(O)SEt SO₂Me 1617 Et Me Et Me OC(O)SEt SO₂Me 1618 Me Me Me Me OC(O)SEt SO₂Me 1619 Et Me Me Me OC(O)SEt SO₂Me 1620 Me Me Et Me OCH₂CH₂OMe SO₂Me 1621 Me Me Me Me OCH₂CH₂OMe SO₂Et 1622 Me Me Et Cl OCH₂CH₂OMe SO₂Me 1623 Et Me Et Me OEt SO₂Me 1624 Et Me Et Cl CO₂Et SO₂Me 1625 Et Me Et Cl CO₂(n-Pr) SO₂Me 1626 Et Me Et Me CO₂Et SO₂Me 1627 Et Me Me Me CO₂Et SO₂Me 1628 Me Me Et Me CH₂OMe SO₂Me 1629 Me Me Et Me CH₂CO₂Me SO₂Me 1630 Me Me Et Me OCH₂CO₂Et SO₂Me 1631 Me Me Et Me O(n-Pr) SO₂Me 1632 Et Me Et Me O(n-Pr) SO₂Me 1633 Et Me Et SO₂Me H CF₃ 1634 Me Me Et Me CH₂OCH₂CF₃ SO₂Me 1635 Me Me Et Cl CH₂OCH₂CF₃ SO₂Me 1636 Et Me Et Me Cl SO₂Me 1637 Me Me Et Me CH₂SO₂Me SO₂Me 1638 Me Me Et Me CH₂OEt SO₂Me 1639 Me Me Me Cl CH₂OMe SO₂Me 1640 Me Me Et Me CH₂CH₂OMe SO₂Me 1641 Me Me Et Me CH₂OCH₂CH₂OMe SO₂Me 1642 Me Me Et Me OCH₂CH₂OEt SO₂Me 1643 Me Me Et Me OCH₂CH₂Cl SO₂Me 1644 Me Me Et Me OCH₂CF₃ SO₂Me 1645 Me Me Et Me CH₂OCH₂OMe SO₂Me 1646 Me Me Et Me OCH₂CH₂SMe SO₂Me 1647 Me Me Et Me CN SO₂Me 1648 Me Me Et Me CH₂CN SO₂Me 1649 Me Me n-Pr Me CO₂Me SO₂Me 1650 Et Me n-Pr Me CO₂Me SO₂Me 1651 Me Me i-Pr Me CO₂Me SO₂Me 1652 Et Me i-Pr Me CO₂Me SO₂Me 1653 Me Me s-Bu Me CO₂Me SO₂Me 1654 Et Me s-Bu Me CO₂Me SO₂Me 1655 Me Me Bn Me CO₂Me SO₂Me 1656 Et Me Bn Me CO₂Me SO₂Me 1657 Me Me Et Br CO₂Me SO₂Me 1658 Et Me Et Cl CO₂Me SO₂Me 1659 Me Me Me Br CO₂Me SO₂Me 1660 Et Me Me Cl CO₂Me SO₂Me 1661 Me Me Allyl Me CO₂Me SO₂Me 1662 Et Me Allyl Me CO₂Me SO₂Me 1663 Me Me CH₂CH(CH₃)═CH₂ Me CO₂Me SO₂Me 1664 Et Me CH₂CH(CH₃)═CH₂ Me CO₂Me SO₂Me 1665 Me Me Et Cl OCH₂CH₂OCF₃ SO₂Me 1666 Et Me Et Cl OCH₂CH₂OCF₃ SO₂Me 1667 Me Me Et Me OCH₂CH₂OCF₃ SO₂Me 1668 Et Me Et Me OCH₂CH₂OCF₃ SO₂Me 1669 Me Me Et CF₃ OCH₂CH₂OCF₃ SO₂Me 1670 Et Me Et CF₃ OCH₂CH₂OCF₃ SO₂Me 1671 Me Me Et Br OCH₂CH₂OCF₃ SO₂Me 1672 Et Me Et Br OCH₂CH₂OCF₃ SO₂Me 1673 Me Me Et SO₂Me OCH₂CH₂OCF₃ SO₂Me 1674 Et Me Et SO₂Me OCH₂CH₂OCF₃ SO₂Me 1675 Me Me Et Cl OCH₂CH₂OCHClF SO₂Me 1676 Et Me Et Cl OCH₂CH₂OCHClF SO₂Me 1677 Me Me Et Me OCH₂CH₂OCHClF SO₂Me 1678 Et Me Et Me OCH₂CH₂OCHClF SO₂Me 1679 Me Me Et CF₃ OCH₂CH₂OCHClF SO₂Me 1680 Et Me Et CF₃ OCH₂CH₂OCHClF SO₂Me 1681 Me Me Et Br OCH₂CH₂OCHClF SO₂Me 1682 Et Me Et Br OCH₂CH₂OCHClF SO₂Me 1683 Me Me Et SO₂Me OCH₂CH₂OCHClF CF₃ 1684 Et Me Et SO₂Me OCH₂CH₂OCHClF CF₃ 1685 Me Me Et Cl OCH₂CHFOCF₃ SO₂Me 1686 Et Me Et Cl OCH₂CHFOCF₃ SO₂Me 1687 Me Me Et Me OCH₂CHFOCF₃ SO₂Me 1688 Me Me Et Cl OCH₂CHFOMe SO₂Me 1689 Et Me Et Cl OCH₂CHFOMe SO₂Me 1690 Me Me Et Me OCH₂CHFOMe SO₂Me 1691 Et Me Et Me OCH₂CHFOMe SO₂Me 1692 Me Me Et CF₃ OCH₂CHFOMe SO₂Me 1693 Et Me Et CF₃ OCH₂CHFOMe SO₂Me 1694 Me Me Et Br OCH₂CHFOMe SO₂Me 1695 Et Me Et Br OCH₂CHFOMe SO₂Me 1696 Me Me Et SO₂Me OCH₂CHFOMe CF₃ 1697 Et Me Et SO₂Me OCH₂CHFOMe CF₃ 1698 Me Me Et Cl OCHFCH₂OCF₃ SO₂Me 1699 Et Me Et Cl OCHFCH₂OCF₃ SO₂Me 1700 Me Me Et Cl OCH₂CH₂OCF₂Cl SO₂Me 1701 Et Me Et Cl OCH₂CH₂OCF₂Cl SO₂Me 1702 Me Me Et Me OCH₂CH₂OCF₂Cl SO₂Me 1703 Et Me Et Me OCH₂CH₂OCF₂Cl SO₂Me 1704 Me Me Et CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1705 Et Me Et CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1706 Me Me Et Br OCH₂CH₂OCF₂Cl SO₂Me 1707 Et Me Et Br OCH₂CH₂OCF₂Cl SO₂Me 1708 Me Me Et SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1709 Et Me Et SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1710 Me Me Et Cl SCH₂CH₂OCH₃ SO₂Me 1711 Et Me Et Cl SCH₂CH₂OCH₃ SO₂Me 1712 Me Me Et Me SCH₂CH₂OCH₃ SO₂Me 1713 Et Me Et Me SCH₂CH₂OCH₃ SO₂Me 1714 Me Me Et CF₃ SCH₂CH₂OCH₃ SO₂Me 1715 Et Me Et CF₃ SCH₂CH₂OCH₃ SO₂Me 1716 Me Me Et Br SCH₂CH₂OCH₃ SO₂Me 1717 Et Me Et Br SCH₂CH₂OCH₃ SO₂Me 1718 Me Me Et SO₂Me SCH₂CH₂OCH₃ CF₃ 1719 Et Me Et SO₂Me SCH₂CH₂OCH₃ CF₃ 1720 Me Me Et Cl SCH₂CH₂OCF₃ SO₂Me 1721 Et Me Et Cl SCH₂CH₂OCF₃ SO₂Me 1722 Me Me Et Me SCH₂CH₂OCF₃ SO₂Me 1723 Et Me Et Me SCH₂CH₂OCF₃ SO₂Me 1724 Me Me Et CF₃ SCH₂CH₂OCF₃ SO₂Me 1725 Et Me Et CF₃ SCH₂CH₂OCF₃ SO₂Me 1726 Me Me Et Br SCH₂CH₂OCF₃ SO₂Me 1727 Et Me Et Br SCH₂CH₂OCF₃ SO₂Me 1728 Me Me Et SO₂Me SCH₂CH₂OCF₃ CF₃ 1729 Et Me Et SO₂Me SCH₂CH₂OCF₃ CF₃ 1730 Me Me Et Cl SCH₂CH₂SCH₃ SO₂Me 1731 Et Me Et Cl SCH₂CH₂SCH₃ SO₂Me 1732 Me Me Et Me SCH₂CH₂SCH₃ SO₂Me 1733 Et Me Et Me SCH₂CH₂SCH₃ SO₂Me 1734 Me Me Et CF₃ SCH₂CH₂SCH₃ SO₂Me 1735 Et Me Et CF₃ SCH₂CH₂SCH₃ SO₂Me 1736 Me Me Et Br SCH₂CH₂SCH₃ SO₂Me 1737 Et Me Et Br SCH₂CH₂SCH₃ SO₂Me 1738 Me Me Et SO₂Me SCH₂CH₂SCH₃ CF₃ 1739 Et Me Et SO₂Me SCH₂CH₂SCH₃ CF₃ 1740 Me Me Et Cl SCH₂CH₂SCF₃ SO₂Me 1741 Et Me Et Cl SCH₂CH₂SCF₃ SO₂Me 1742 Me Me Et Me SCH₂CH₂SCF₃ SO₂Me 1743 Et Me Et Me SCH₂CH₂SCF₃ SO₂Me 1744 Me Me Et CF₃ SCH₂CH₂SCF₃ SO₂Me 1745 Et Me Et CF₃ SCH₂CH₂SCF₃ SO₂Me 1746 Me Me Et Br SCH₂CH₂SCF₃ SO₂Me 1747 Et Me Et Br SCH₂CH₂SCF₃ SO₂Me 1748 Me Me Et SO₂Me SCH₂CH₂SCF₃ CF₃ 1749 Et Me Et SO₂Me SCH₂CH₂SCF₃ CF₃ 1750 Me Me Et Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1751 Et Me Et Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1752 Me Me Et Me OCH₂CH(CH₃)OCH₃ SO₂Me 1753 Et Me Et Me OCH₂CH(CH₃)OCH₃ SO₂Me 1754 Me Me Et CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1755 Et Me Et CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1756 Me Me Et Br OCH₂CH(CH₃)OCH₃ SO₂Me 1757 Et Me Et Br OCH₂CH(CH₃)OCH₃ SO₂Me 1758 Me Me Et SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1759 Et Me Et SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1760 Me Me Et Cl OCH₂CF₂OCH₃ SO₂Me 1761 Et Me Et Cl OCH₂CF₂OCH₃ SO₂Me 1762 Me Me Et Me OCH₂CF₂OCH₃ SO₂Me 1763 Et Me Et Me OCH₂CF₂OCH₃ SO₂Me 1764 Me Me Et CF₃ OCH₂CF₂OCH₃ SO₂Me 1765 Et Me Et CF₃ OCH₂CF₂OCH₃ SO₂Me 1766 Me Me Et Br OCH₂CF₂OCH₃ SO₂Me 1767 Et Me Et Br OCH₂CF₂OCH₃ SO₂Me 1768 Me Me Et SO₂Me OCH₂CF₂OCH₃ CF₃ 1769 Et Me Et SO₂Me OCH₂CF₂OCH₃ CF₃ 1770 Me Me i-Pr Me OCH₂CH₂OCH₃ SO₂Me 1771 Et Me i-Pr Me OCH₂CH₂OCH₃ SO₂Me 1772 Me Me Et Me OCH₂CH(OCH₃)₂ SO₂Me 1773 Me Me Et Me CH₂N(Me)CH₂CN SO₂Me 1774 Me Me Et Me (tetrahydrofuran-2-yl)methoxy SO₂Me 1775 Me Me Et Cl SMe SO₂Me 1776 Me Me Et Cl Cl SO₂Me 1777 Me Me Et Cl OMe SO₂Me 1778 Me Me Et Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 1779 Me Me Et CN OCH₂CH₂OMe SO₂Me 1780 Me Me Et Me tetrahydrofuran-3-yloxy SO₂Me 1781 Me Me Et Me OCH₂CH₂CH₂OMe SO₂Me 1782 Me Me n-Pr Me OCH₂CH₂OMe SO₂Me 1783 Et Me s-Bu Cl C(O)OMe SO₂Me 1784 Et Me Et Cl 2-(1,3-dioxolan-2-yl)ethoxy SO₂Me 1785 Me Me Et Me propargyloxy SO₂Me 1786 Me Me Et Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 1787 Me Me Et Cl SO₂Me SO₂Me 1788 Me Me Et Me (CH₂)₆Me SO₂Me 1789 Me Me Et Me CH₂CH₂CH₂OMe SO₂Me 1790 Et Me Et Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 1791 Me Me Et Me CH₂N[C(O)SEt]CH₂CN SO₂Me 1792 Me Me Et Me CH═CHCN SO₂Me 1793 Me Me Et Me CH₂CH₂CN SO₂Me 1794 Me Me Et Me CH₂SCN SO₂Me 1795 Me Me Et Me CH₂C(S)NH₂ SO₂Me 1796 Me Me Me Me OCH₂CH₂OMe SO₂Me 1797 Et Me Me Me OCH₂CH₂OMe SO₂Me 1798 Et Me n-Pr Me OCH₂CH₂OMe SO₂Me 1799 Me Me Et Me OCH(CH₃)CH₂OMe SO₂Me 1800 Et Me Et Me OCH₂CH(Et)OMe SO₂Me 1801 Me Me Et Me (1,3-dioxolan-2-yl)methyl SO₂Me 1802 Me Me s-Bu Me OCH₂CH₂OMe SO₂Me 1803 Me Me Et Me CH₂O(i-Pr) SO₂Me 1804 Me H CH₂CF₃ Cl CO₂Et SO₂Me 1805 Et H CH₂CF₃ Me CO₂Me CF₃ 1806 Et H CH₂CF₃ SO₂Me CO₂Me CN 1807 Me H CH₂CF₃ Me C(O)SMe SO₂Me 1808 Me H CH₂CF₃ Me C(O)SEt SO₂Me 1809 Me H CH₂CF₃ Me 2-(2-oxolanyl)ethoxy SO₂Me 1810 Me H CH₂CF₃ Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 1811 Et H CH₂CF₃ Me CH₂OMe SO₂Me 1812 Et H CH₂CF₃ Me 2-oxolanylmethoxymethyl SO₂Me 1813 Me H CH₂CF₃ Cl CO₂Me SO₂Me 1814 Et H CH₂CF₃ Cl CO₂Me SO₂Et 1815 Me H CH₂CF₃ Cl C(O)SMe SO₂Me 1816 Me H CH₂CF₃ Cl C(O)SEt SO₂Me 1817 Me H CH₂CF₃ Me OMe SO₂Me 1818 Me H CH₂CF₃ Me OEt SO₂Me 1819 Me H CH₂CF₃ Me O(i-Pr) SO₂Me 1820 Me H CH₂CF₃ Me OCHF₂ SO₂Me 1821 Me H CH₂CF₃ Me (4,5-dihydroisoxazol-3-yl) SO₂Me 1822 Me H CH₂CF₃ Me O(n-Pr) SO₂Et 1823 Me H CH₂CF₃ Cl CH₂OMe SO₂Me 1824 Me H CH₂CF₃ Me OCO₂Me SO₂Me 1825 Me H CH₂CF₃ Me OC(O)SMe SO₂Me 1826 Me H CH₂CF₃ Me OC(O)SEt SO₂Me 1827 Et H CH₂CF₃ Me OEt SO₂Me 1828 Et H CH₂CF₃ Cl CO₂Et SO₂Me 1829 Et H CH₂CF₃ Cl CO₂(n-Pr) SO₂Me 1830 Et H CH₂CF₃ Me CO₂Et SO₂Me 1831 Me H CH₂CF₃ Me CH₂CO₂Me SO₂Me 1832 Me H CH₂CF₃ Me OCH₂CO₂Et SO₂Me 1833 Me H CH₂CF₃ Me O(n-Pr) SO₂Me 1834 Et H CH₂CF₃ SO₂Me H CF₃ 1835 Me H CH₂CF₃ Me CH₂OCH₂CF₃ SO₂Me 1836 Me H CH₂CF₃ Cl CH₂OCH₂CF₃ SO₂Me 1837 Et H CH₂CF₃ Me Cl SO₂Me 1838 Me H CH₂CF₃ Me CH₂SO₂Me SO₂Me 1839 Me H CH₂CF₃ Me CH₂OEt SO₂Me 1840 Me H CH₂CF₃ Cl CH₂OMe SO₂Me 1841 Me H CH₂CF₃ Me CH₂CH₂OMe SO₂Me 1842 Me H CH₂CF₃ Me CH₂OCH₂CH₂OMe SO₂Me 1843 Me H CH₂CF₃ Me OCH₂CH₂OEt SO₂Me 1844 Me H CH₂CF₃ Me OCH₂CH₂Cl SO₂Me 1845 Me H CH₂CF₃ Me OCH₂CF₃ SO₂Me 1846 Me H CH₂CF₃ Me CH₂OCH₂OMe SO₂Me 1847 Me H CH₂CF₃ Me OCH₂CH₂SMe SO₂Me 1848 Me H CH₂CF₃ Me CN SO₂Me 1849 Me H CH₂CF₃ Me CH₂CN SO₂Me 1850 Me H CH₂CF₃ Br CO₂Me SO₂Me 1851 Et H CH₂CF₃ Cl CO₂Me SO₂Me 1852 Me H CH₂CF₃ CN CO₂Me SO₂Me 1853 Me H CH₂CF₃ Cl OCH₂CH₂OCF₃ SO₂Me 1854 Et H CH₂CF₃ Cl OCH₂CH₂OCF₃ SO₂Me 1855 Me H CH₂CF₃ Me OCH₂CH₂OCF₃ SO₂Me 1856 Et H CH₂CF₃ Me OCH₂CH₂OCF₃ SO₂Me 1857 Me H CH₂CF₃ CF₃ OCH₂CH₂OCF₃ SO₂Me 1858 Et H CH₂CF₃ CF₃ OCH₂CH₂OCF₃ SO₂Me 1859 Me H CH₂CF₃ Br OCH₂CH₂OCF₃ SO₂Me 1860 Et H CH₂CF₃ Br OCH₂CH₂OCF₃ SO₂Me 1861 Me H CH₂CF₃ SO₂Me OCH₂CH₂OCF₃ CF₃ 1862 Et H CH₂CF₃ SO₂Me OCH₂CH₂OCF₃ CF₃ 1863 Me H CH₂CF₃ Cl OCH₂CH₂OCHClF SO₂Me 1864 Et H CH₂CF₃ Cl OCH₂CH₂OCHClF SO₂Me 1865 Me H CH₂CF₃ Me OCH₂CH₂OCHClF SO₂Me 1866 Et H CH₂CF₃ Me OCH₂CH₂OCHClF SO₂Me 1867 Me H CH₂CF₃ CF₃ OCH₂CH₂OCHClF SO₂Me 1868 Et H CH₂CF₃ CF₃ OCH₂CH₂OCHClF SO₂Me 1869 Me H CH₂CF₃ Br OCH₂CH₂OCHClF SO₂Me 1870 Et H CH₂CF₃ Br OCH₂CH₂OCHClF SO₂Me 1871 Me H CH₂CF₃ SO₂Me OCH₂CH₂OCHClF CF₃ 1872 Et H CH₂CF₃ SO₂Me OCH₂CH₂OCHClF CF₃ 1873 Me H CH₂CF₃ Cl OCH₂CHFOCF₃ CF₃ 1874 Et H CH₂CF₃ Cl OCH₂CHFOCF₃ CF₃ 1875 Me H CH₂CF₃ Me OCH₂CHFOCF₃ SO₂Me 1876 Me H CH₂CF₃ Cl OCH₂CHFOMe SO₂Me 1877 Et H CH₂CF₃ Cl OCH₂CHFOMe SO₂Me 1878 Me H CH₂CF₃ Me OCH₂CHFOMe SO₂Me 1879 Et H CH₂CF₃ Me OCH₂CHFOMe SO₂Me 1880 Me H CH₂CF₃ CF₃ OCH₂CHFOMe SO₂Me 1881 Et H CH₂CF₃ CF₃ OCH₂CHFOMe SO₂Me 1882 Me H CH₂CF₃ Br OCH₂CHFOMe SO₂Me 1883 Et H CH₂CF₃ Br OCH₂CHFOMe SO₂Me 1884 Me H CH₂CF₃ SO₂Me OCH₂CHFOMe CF₃ 1885 Et H CH₂CF₃ SO₂Me OCH₂CHFOMe CF₃ 1886 Me H CH₂CF₃ Cl OCHFCH₂OCF₃ SO₂Me 1887 Et H CH₂CF₃ Cl OCHFCH₂OCF₃ SO₂Me 1888 Me H CH₂CF₃ Cl OCH₂CH₂OCF₂Cl SO₂Me 1889 Et H CH₂CF₃ Cl OCH₂CH₂OCF₂Cl SO₂Me 1890 Me H CH₂CF₃ Me OCH₂CH₂OCF₂Cl SO₂Me 1891 Et H CH₂CF₃ Me OCH₂CH₂OCF₂Cl SO₂Me 1892 Me H CH₂CF₃ CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1893 Et H CH₂CF₃ CF₃ OCH₂CH₂OCF₂Cl SO₂Me 1894 Me H CH₂CF₃ Br OCH₂CH₂OCF₂Cl SO₂Me 1895 Et H CH₂CF₃ Br OCH₂CH₂OCF₂Cl SO₂Me 1896 Me H CH₂CF₃ SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1897 Et H CH₂CF₃ SO₂Me OCH₂CH₂OCF₂Cl CF₃ 1898 Me H CH₂CF₃ Cl SCH₂CH₂OCH₃ SO₂Me 1899 Et H CH₂CF₃ Cl SCH₂CH₂OCH₃ SO₂Me 1900 Me H CH₂CF₃ Me SCH₂CH₂OCH₃ SO₂Me 1901 Et H CH₂CF₃ Me SCH₂CH₂OCH₃ SO₂Me 1902 Me H CH₂CF₃ CF₃ SCH₂CH₂OCH₃ SO₂Me 1903 Et H CH₂CF₃ CF₃ SCH₂CH₂OCH₃ SO₂Me 1904 Me H CH₂CF₃ Br SCH₂CH₂OCH₃ SO₂Me 1905 Et H CH₂CF₃ Br SCH₂CH₂OCH₃ SO₂Me 1906 Me H CH₂CF₃ SO₂Me SCH₂CH₂OCH₃ CF₃ 1907 Et H CH₂CF₃ SO₂Me SCH₂CH₂OCH₃ CF₃ 1908 Me H CH₂CF₃ Cl SCH₂CH₂OCF₃ SO₂Me 1909 Et H CH₂CF₃ Cl SCH₂CH₂OCF₃ SO₂Me 1910 Me H CH₂CF₃ Me SCH₂CH₂OCF₃ SO₂Me 1911 Et H CH₂CF₃ Me SCH₂CH₂OCF₃ SO₂Me 1912 Me H CH₂CF₃ CF₃ SCH₂CH₂OCF₃ SO₂Me 1913 Et H CH₂CF₃ CF₃ SCH₂CH₂OCF₃ SO₂Me 1914 Me H CH₂CF₃ Br SCH₂CH₂OCF₃ SO₂Me 1915 Et H CH₂CF₃ Br SCH₂CH₂OCF₃ SO₂Me 1916 Me H CH₂CF₃ SO₂Me SCH₂CH₂OCF₃ CF₃ 1917 Et H CH₂CF₃ SO₂Me SCH₂CH₂OCF₃ CF₃ 1918 Me H CH₂CF₃ Cl SCH₂CH₂SCH₃ SO₂Me 1919 Et H CH₂CF₃ Cl SCH₂CH₂SCH₃ SO₂Me 1920 Me H CH₂CF₃ Me SCH₂CH₂SCH₃ SO₂Me 1921 Et H CH₂CF₃ Me SCH₂CH₂SCH₃ SO₂Me 1922 Me H CH₂CF₃ CF₃ SCH₂CH₂SCH₃ SO₂Me 1923 Et H CH₂CF₃ CF₃ SCH₂CH₂SCH₃ SO₂Me 1924 Me H CH₂CF₃ Br SCH₂CH₂SCH₃ SO₂Me 1925 Et H CH₂CF₃ Br SCH₂CH₂SCH₃ SO₂Me 1926 Me H CH₂CF₃ SO₂Me SCH₂CH₂SCH₃ CF₃ 1927 Et H CH₂CF₃ SO₂Me SCH₂CH₂SCH₃ CF₃ 1928 Me H CH₂CF₃ Cl SCH₂CH₂SCF₃ SO₂Me 1929 Et H CH₂CF₃ Cl SCH₂CH₂SCF₃ SO₂Me 1930 Me H CH₂CF₃ Me SCH₂CH₂SCF₃ SO₂Me 1931 Et H CH₂CF₃ Me SCH₂CH₂SCF₃ SO₂Me 1932 Me H CH₂CF₃ CF₃ SCH₂CH₂SCF₃ SO₂Me 1933 Et H CH₂CF₃ CF₃ SCH₂CH₂SCF₃ SO₂Me 1934 Me H CH₂CF₃ Br SCH₂CH₂SCF₃ SO₂Me 1935 Et H CH₂CF₃ Br SCH₂CH₂SCF₃ SO₂Me 1936 Me H CH₂CF₃ SO₂Me SCH₂CH₂SCF₃ CF₃ 1937 Et H CH₂CF₃ SO₂Me SCH₂CH₂SCF₃ CF₃ 1938 Me H CH₂CF₃ Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1939 Et H CH₂CF₃ Cl OCH₂CH(CH₃)OCH₃ SO₂Me 1940 Me H CH₂CF₃ Me OCH₂CH(CH₃)OCH₃ SO₂Me 1941 Et H CH₂CF₃ Me OCH₂CH(CH₃)OCH₃ SO₂Me 1942 Me H CH₂CF₃ CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1943 Et H CH₂CF₃ CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 1944 Me H CH₂CF₃ Br OCH₂CH(CH₃)OCH₃ SO₂Me 1945 Et H CH₂CF₃ Br OCH₂CH(CH₃)OCH₃ SO₂Me 1946 Me H CH₂CF₃ SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1947 Et H CH₂CF₃ SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 1948 Me H CH₂CF₃ Cl OCH₂CF₂OCH₃ SO₂Me 1949 Et H CH₂CF₃ Cl OCH₂CF₂OCH₃ SO₂Me 1950 Me H CH₂CF₃ Me OCH₂CF₂OCH₃ SO₂Me 1951 Et H CH₂CF₃ Me OCH₂CF₂OCH₃ SO₂Me 1952 Me H CH₂CF₃ CF₃ OCH₂CF₂OCH₃ SO₂Me 1953 Et H CH₂CF₃ CF₃ OCH₂CF₂OCH₃ SO₂Me 1954 Me H CH₂CF₃ Br OCH₂CF₂OCH₃ SO₂Me 1955 Et H CH₂CF₃ Br OCH₂CF₂OCH₃ SO₂Me 1956 Me H CH₂CF₃ SO₂Me OCH₂CF₂OCH₃ CF₃ 1957 Et H CH₂CF₃ SO₂Me OCH₂CF₂OCH₃ CF₃ 1958 Me H CH₂CF₃ Me OCH₂CH₂OCH₃ SO₂Me 1959 Et H CH₂CF₃ Me OCH₂CH₂OCH₃ SO₂Me 1960 Me H CH₂CF₃ Me OCH₂CH(OCH₃)₂ SO₂Me 1961 Me H CH₂CF₃ Me CH₂N(Me)CH₂CN SO₂Me 1962 Me H CH₂CF₃ Me (tetrahydrofuran-2-yl)methoxy SO₂Me 1963 Me H CH₂CF₃ Cl SMe SO₂Me 1964 Me H CH₂CF₃ Cl Cl SO₂Me 1965 Me H CH₂CF₃ Cl OMe SO₂Me 1966 Me H CH₂CF₃ Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 1967 Me H CH₂CF₃ Cl OCH₂CH₂OMe SO₂Me 1968 Me H CH₂CF₃ Me tetrahydrofuran-3-yloxy SO₂Me 1969 Me H CH₂CF₃ Me OCH₂CH₂CH₂OMe SO₂Me 1970 Me H CH₂CF₃ Me OCH₂CH₂OMe SO₂Me 1971 Et H CH₂CF₃ Cl 2-(1,3-dioxolan-2-yl)ethoxy SO₂Me 1972 Me H CH₂CF₃ Me propargyloxy SO₂Me 1973 Me H CH₂CF₃ Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 1974 Me H CH₂CF₃ Cl SO₂Me SO₂Me 1975 Me H CH₂CF₃ Me (CH₂)₆Me SO₂Me 1976 Me H CH₂CF₃ Me CH₂CH₂CH₂OMe SO₂Me 1977 Et H CH₂CF₃ Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 1978 Me H CH₂CF₃ Me CH₂N[C(O)SEt]CH₂CN SO₂Me 1979 Me H CH₂CF₃ Me CH═CHCN SO₂Me 1980 Me H CH₂CF₃ Me CH₂CH₂CN SO₂Me 1981 Me H CH₂CF₃ Me CH₂SCN SO₂Me 1982 Me H CH₂CF₃ Me CH₂C(S)NH₂ SO₂Me 1983 Me H CH₂CF₃ CN OCH₂CH₂OMe SO₂Me 1984 Et H CH₂CF₃ Me OCH₂CH₂OMe SO₂Me 1985 Me H CH₂CF₃ Me OCH(CH₃)CH₂OMe SO₂Me 1986 Et H CH₂CF₃ Me OCH₂CH(Et)OMe SO₂Me 1987 Me H CH₂CF₃ Me (1,3-dioxolan-2-yl)methyl SO₂Me 1988 Me H CH₂CF₃ Me CH₂O(i-Pr) SO₂Me 1989 Me H CH₂CHF₂ Cl CO₂Et SO₂Me 1990 Et H CH₂CHF₂ Me CO₂Me CF₃ 1991 Et H CH₂CHF₂ SO₂Me CO₂Me CN 1992 Me H CH₂CHF₂ Me C(O)SMe SO₂Me 1993 Me H CH₂CHF₂ Me C(O)SEt SO₂Me 1994 Me H CH₂CHF₂ Me 2-(2-oxolanyl)ethoxy SO₂Me 1995 Me H CH₂CHF₂ Me 2-(2-(1,3-dioxolanyl))ethoxy SO₂Me 1996 Et H CH₂CHF₂ Me CH₂OMe SO₂Me 1997 Et H CH₂CHF₂ Me 2-oxolanylmethoxymethyl SO₂Me 1998 Me H CH₂CHF₂ Cl CO₂Me SO₂Me 1999 Et H CH₂CHF₂ Cl CO₂Me SO₂Et 2000 Me H CH₂CHF₂ Cl C(O)SMe SO₂Me 2001 Me H CH₂CHF₂ Cl C(O)SEt SO₂Me 2002 Me H CH₂CHF₂ Me OMe SO₂Me 2003 Me H CH₂CHF₂ Me OEt SO₂Me 2004 Me H CH₂CHF₂ Me O(i-Pr) SO₂Me 2005 Me H CH₂CHF₂ Me OCHF₂ SO₂Me 2006 Me H CH₂CHF₂ Me (4,5-dihydroisoxazol-3-yl) SO₂Me 2007 Me H CH₂CHF₂ Me O(n-Pr) SO₂Et 2008 Me H CH₂CHF₂ Cl CH₂OMe SO₂Me 2009 Me H CH₂CHF₂ Me OCO₂Me SO₂Me 2010 Me H CH₂CHF₂ Me OC(O)SMe SO₂Me 2011 Me H CH₂CHF₂ Me OC(O)SEt SO₂Me 2012 Et H CH₂CHF₂ Me OEt SO₂Me 2013 Et H CH₂CHF₂ Cl CO₂Et SO₂Me 2014 Et H CH₂CHF₂ Cl CO₂(n-Pr) SO₂Me 2015 Et H CH₂CHF₂ Me CO₂Et SO₂Me 2016 Me H CH₂CHF₂ Me CH₂CO₂Me SO₂Me 2017 Me H CH₂CHF₂ Me OCH₂CO₂Et SO₂Me 2018 Me H CH₂CHF₂ Me O(n-Pr) SO₂Me 2019 Et H CH₂CHF₂ SO₂Me H CF₃ 2020 Me H CH₂CHF₂ Me CH₂OCH₂CF₃ SO₂Me 2021 Me H CH₂CHF₂ Cl CH₂OCH₂CF₃ SO₂Me 2022 Et H CH₂CHF₂ Me Cl SO₂Me 2023 Me H CH₂CHF₂ Me CH₂SO₂Me SO₂Me 2024 Me H CH₂CHF₂ Me CH₂OEt SO₂Me 2025 Me H CH₂CHF₂ Cl CH₂OMe SO₂Me 2026 Me H CH₂CHF₂ Me CH₂CH₂OMe SO₂Me 2027 Me H CH₂CHF₂ Me CH₂OCH₂CH₂OMe SO₂Me 2028 Me H CH₂CHF₂ Me OCH₂CH₂OEt SO₂Me 2029 Me H CH₂CHF₂ Me OCH₂CH₂Cl SO₂Me 2030 Me H CH₂CHF₂ Me OCH₂CF₃ SO₂Me 2031 Me H CH₂CHF₂ Me CH₂OCH₂OMe SO₂Me 2032 Me H CH₂CHF₂ Me OCH₂CH₂SMe SO₂Me 2033 Me H CH₂CHF₂ Me CN SO₂Me 2034 Me H CH₂CHF₂ Me CH₂CN SO₂Me 2035 Me H CH₂CHF₂ Br CO₂Me SO₂Me 2036 Et H CH₂CHF₂ Cl CO₂Me SO₂Me 2037 Me H CH₂CHF₂ CN CO₂Me SO₂Me 2038 Me H CH₂CHF₂ Cl OCH₂CH₂OCF₃ SO₂Me 2039 Et H CH₂CHF₂ Cl OCH₂CH₂OCF₃ SO₂Me 2040 Me H CH₂CHF₂ Me OCH₂CH₂OCF₃ SO₂Me 2041 Et H CH₂CHF₂ Me OCH₂CH₂OCF₃ SO₂Me 2042 Me H CH₂CHF₂ CF₃ OCH₂CH₂OCF₃ SO₂Me 2043 Et H CH₂CHF₂ CF₃ OCH₂CH₂OCF₃ SO₂Me 2044 Me H CH₂CHF₂ Br OCH₂CH₂OCF₃ SO₂Me 2045 Et H CH₂CHF₂ Br OCH₂CH₂OCF₃ SO₂Me 2046 Me H CH₂CHF₂ SO₂Me OCH₂CH₂OCF₃ CF₃ 2047 Et H CH₂CHF₂ SO₂Me OCH₂CH₂OCF₃ CF₃ 2048 Me H CH₂CHF₂ Cl OCH₂CH₂OCHClF SO₂Me 2049 Et H CH₂CHF₂ Cl OCH₂CH₂OCHClF SO₂Me 2050 Me H CH₂CHF₂ Me OCH₂CH₂OCHClF SO₂Me 2051 Et H CH₂CHF₂ Me OCH₂CH₂OCHClF SO₂Me 2052 Me H CH₂CHF₂ CF₃ OCH₂CH₂OCHClF SO₂Me 2053 Et H CH₂CHF₂ CF₃ OCH₂CH₂OCHClF SO₂Me 2054 Me H CH₂CHF₂ Br OCH₂CH₂OCHClF SO₂Me 2055 Et H CH₂CHF₂ Br OCH₂CH₂OCHClF SO₂Me 2056 Me H CH₂CHF₂ SO₂Me OCH₂CH₂OCHClF CF₃ 2057 Et H CH₂CHF₂ SO₂Me OCH₂CH₂OCHClF CF₃ 2058 Me H CH₂CHF₂ Cl OCH₂CHFOCF₃ SO₂Me 2059 Et H CH₂CHF₂ Cl OCH₂CHFOCF₃ SO₂Me 2060 Me H CH₂CHF₂ Me OCH₂CHFOCF₃ SO₂Me 2061 Me H CH₂CHF₂ Cl OCH₂CHFOMe SO₂Me 2062 Et H CH₂CHF₂ Cl OCH₂CHFOMe SO₂Me 2063 Me H CH₂CHF₂ Me OCH₂CHFOMe SO₂Me 2064 Et H CH₂CHF₂ Me OCH₂CHFOMe SO₂Me 2065 Me H CH₂CHF₂ CF₃ OCH₂CHFOMe SO₂Me 2066 Et H CH₂CHF₂ CF₃ OCH₂CHFOMe SO₂Me 2067 Me H CH₂CHF₂ Br OCH₂CHFOMe SO₂Me 2068 Et H CH₂CHF₂ Br OCH₂CHFOMe SO₂Me 2069 Me H CH₂CHF₂ SO₂Me OCH₂CHFOMe CF₃ 2070 Et H CH₂CHF₂ SO₂Me OCH₂CHFOMe CF₃ 2071 Me H CH₂CHF₂ Cl OCHFCH₂OCF₃ SO₂Me 2072 Et H CH₂CHF₂ Cl OCHFCH₂OCF₃ SO₂Me 2073 Me H CH₂CHF₂ Cl OCH₂CH₂OCF₂Cl SO₂Me 2074 Et H CH₂CHF₂ Cl OCH₂CH₂OCF₂Cl SO₂Me 2075 Me H CH₂CHF₂ Me OCH₂CH₂OCF₂Cl SO₂Me 2076 Et H CH₂CHF₂ Me OCH₂CH₂OCF₂Cl SO₂Me 2077 Me H CH₂CHF₂ CF₃ OCH₂CH₂OCF₂Cl SO₂Me 2078 Et H CH₂CHF₂ CF₃ OCH₂CH₂OCF₂Cl SO₂Me 2079 Me H CH₂CHF₂ Br OCH₂CH₂OCF₂Cl SO₂Me 2080 Et H CH₂CHF₂ Br OCH₂CH₂OCF₂Cl SO₂Me 2081 Me H CH₂CHF₂ SO₂Me OCH₂CH₂OCF₂Cl CF₃ 2082 Et H CH₂CHF₂ SO₂Me OCH₂CH₂OCF₂Cl CF₃ 2083 Me H CH₂CHF₂ Cl SCH₂CH₂OCH₃ SO₂Me 2084 Et H CH₂CHF₂ Cl SCH₂CH₂OCH₃ SO₂Me 2085 Me H CH₂CHF₂ Me SCH₂CH₂OCH₃ SO₂Me 2086 Et H CH₂CHF₂ Me SCH₂CH₂OCH₃ SO₂Me 2087 Me H CH₂CHF₂ CF₃ SCH₂CH₂OCH₃ SO₂Me 2088 Et H CH₂CHF₂ CF₃ SCH₂CH₂OCH₃ SO₂Me 2089 Me H CH₂CHF₂ Br SCH₂CH₂OCH₃ SO₂Me 2090 Et H CH₂CHF₂ Br SCH₂CH₂OCH₃ SO₂Me 2091 Me H CH₂CHF₂ SO₂Me SCH₂CH₂OCH₃ CF₃ 2092 Et H CH₂CHF₂ SO₂Me SCH₂CH₂OCH₃ CF₃ 2093 Me H CH₂CHF₂ Cl SCH₂CH₂OCF₃ SO₂Me 2094 Et H CH₂CHF₂ Cl SCH₂CH₂OCF₃ SO₂Me 2095 Me H CH₂CHF₂ Me SCH₂CH₂OCF₃ SO₂Me 2096 Et H CH₂CHF₂ Me SCH₂CH₂OCF₃ SO₂Me 2097 Me H CH₂CHF₂ CF₃ SCH₂CH₂OCF₃ SO₂Me 2098 Et H CH₂CHF₂ CF₃ SCH₂CH₂OCF₃ SO₂Me 2099 Me H CH₂CHF₂ Br SCH₂CH₂OCF₃ SO₂Me 2100 Et H CH₂CHF₂ Br SCH₂CH₂OCF₃ SO₂Me 2101 Me H CH₂CHF₂ SO₂Me SCH₂CH₂OCF₃ CF₃ 2102 Et H CH₂CHF₂ SO₂Me SCH₂CH₂OCF₃ CF₃ 2103 Me H CH₂CHF₂ Cl SCH₂CH₂SCH₃ SO₂Me 2104 Et H CH₂CHF₂ Cl SCH₂CH₂SCH₃ SO₂Me 2105 Me H CH₂CHF₂ Me SCH₂CH₂SCH₃ SO₂Me 2106 Et H CH₂CHF₂ Me SCH₂CH₂SCH₃ SO₂Me 2107 Me H CH₂CHF₂ CF₃ SCH₂CH₂SCH₃ SO₂Me 2108 Et H CH₂CHF₂ CF₃ SCH₂CH₂SCH₃ SO₂Me 2109 Me H CH₂CHF₂ Br SCH₂CH₂SCH₃ SO₂Me 2110 Et H CH₂CHF₂ Br SCH₂CH₂SCH₃ SO₂Me 2111 Me H CH₂CHF₂ SO₂Me SCH₂CH₂SCH₃ CF₃ 2112 Et H CH₂CHF₂ SO₂Me SCH₂CH₂SCH₃ CF₃ 2113 Me H CH₂CHF₂ Cl SCH₂CH₂SCF₃ SO₂Me 2114 Et H CH₂CHF₂ Cl SCH₂CH₂SCF₃ SO₂Me 2115 Me H CH₂CHF₂ Me SCH₂CH₂SCF₃ SO₂Me 2116 Et H CH₂CHF₂ Me SCH₂CH₂SCF₃ SO₂Me 2117 Me H CH₂CHF₂ CF₃ SCH₂CH₂SCF₃ SO₂Me 2118 Et H CH₂CHF₂ CF₃ SCH₂CH₂SCF₃ SO₂Me 2119 Me H CH₂CHF₂ Br SCH₂CH₂SCF₃ SO₂Me 2120 Et H CH₂CHF₂ Br SCH₂CH₂SCF₃ SO₂Me 2121 Me H CH₂CHF₂ SO₂Me SCH₂CH₂SCF₃ CF₃ 2122 Et H CH₂CHF₂ SO₂Me SCH₂CH₂SCF₃ CF₃ 2123 Me H CH₂CHF₂ Cl OCH₂CH(CH₃)OCH₃ SO₂Me 2124 Et H CH₂CHF₂ Cl OCH₂CH(CH₃)OCH₃ SO₂Me 2125 Me H CH₂CHF₂ Me OCH₂CH(CH₃)OCH₃ SO₂Me 2126 Et H CH₂CHF₂ Me OCH₂CH(CH₃)OCH₃ SO₂Me 2127 Me H CH₂CHF₂ CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 2128 Et H CH₂CHF₂ CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 2129 Me H CH₂CHF₂ Br OCH₂CH(CH₃)OCH₃ SO₂Me 2130 Et H CH₂CHF₂ Br OCH₂CH(CH₃)OCH₃ SO₂Me 2131 Me H CH₂CHF₂ SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 2132 Et H CH₂CHF₂ SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 2133 Me H CH₂CHF₂ Cl OCH₂CF₂OCH₃ SO₂Me 2134 Et H CH₂CHF₂ Cl OCH₂CF₂OCH₃ SO₂Me 2135 Me H CH₂CHF₂ Me OCH₂CF₂OCH₃ SO₂Me 2136 Et H CH₂CHF₂ Me OCH₂CF₂OCH₃ SO₂Me 2137 Me H CH₂CHF₂ CF₃ OCH₂CF₂OCH₃ SO₂Me 2138 Et H CH₂CHF₂ CF₃ OCH₂CF₂OCH₃ SO₂Me 2139 Me H CH₂CHF₂ Br OCH₂CF₂OCH₃ SO₂Me 2140 Et H CH₂CHF₂ Br OCH₂CF₂OCH₃ SO₂Me 2141 Me H CH₂CHF₂ SO₂Me OCH₂CF₂OCH₃ CF₃ 2142 Et H CH₂CHF₂ SO₂Me OCH₂CF₂OCH₃ CF₃ 2143 Me H CH₂CHF₂ Me OCH₂CH₂OCH₃ SO₂Me 2144 Et H CH₂CHF₂ Me OCH₂CH₂OCH₃ SO₂Me 2145 Me H CH₂CHF₂ Me OCH₂CH(OCH₃)₂ SO₂Me 2146 Me H CH₂CHF₂ Me CH₂N(Me)CH₂CN SO₂Me 2147 Me H CH₂CHF₂ Me (tetrahydrofuran-2-yl)methoxy SO₂Me 2148 Me H CH₂CHF₂ Cl SMe SO₂Me 2149 Me H CH₂CHF₂ Cl Cl SO₂Me 2150 Me H CH₂CHF₂ Cl OMe SO₂Me 2151 Me H CH₂CHF₂ Me (tetrahydro-2H-pyran-2-yl)methoxy SO₂Me 2152 Me H CH₂CHF₂ Cl OCH₂CH₂OMe SO₂Me 2153 Me H CH₂CHF₂ Me tetrahydrofuran-3-yloxy SO₂Me 2154 Me H CH₂CHF₂ Me OCH₂CH₂CH₂OMe SO₂Me 2155 Me H CH₂CHF₂ CN OCH₂CH₂OMe SO₂Me 2156 Et H CH₂CHF₂ Cl 2-(1,3-dioxolan-2-yl)ethoxy SO₂Me 2157 Me H CH₂CHF₂ Me propargyloxy SO₂Me 2158 Me H CH₂CHF₂ Me (tetrahydrofuran-3-yloxy)methyl SO₂Me 2159 Me H CH₂CHF₂ Cl SO₂Me SO₂Me 2160 Me H CH₂CHF₂ Me (CH₂)₆Me SO₂Me 2161 Me H CH₂CHF₂ Me CH₂CH₂CH₂OMe SO₂Me 2162 Et H CH₂CHF₂ Cl (1,3-dioxolan-2-yl)methoxy SO₂Me 2163 Me H CH₂CHF₂ Me CH₂N[C(O)SEt]CH₂CN SO₂Me 2164 Me H CH₂CHF₂ Me CH═CHCN SO₂Me 2165 Me H CH₂CHF₂ Me CH₂CH₂CN SO₂Me 2166 Me H CH₂CHF₂ Me CH₂SCN SO₂Me 2167 Me H CH₂CHF₂ Me CH₂C(S)NH₂ SO₂Me 2168 Me H CH₂CHF₂ NO₂ OCH₂CH₂OMe SO₂Me 2169 Et H CH₂CHF₂ Me OCH₂CH₂OMe SO₂Me 2170 Me H CH₂CHF₂ Me OCH(CH₃)CH₂OMe SO₂Me 2171 Et H CH₂CHF₂ Me OCH₂CH(Et)OMe SO₂Me 2172 Me H CH₂CHF₂ Me (1,3-dioxolan-2-yl)methyl SO₂Me 2173 Me H CH₂CHF₂ Me CH₂O(i-Pr) SO₂Me

TABLE 2 ¹H-NMR δ ppm (solvent: CDCl₃, measuring instrument: JEOL-GSX(400 MHz) or VARIAN MERCURY plus(300 MHz)/ No. the same applies hereinafter) 1 1.29 (t, 3H), 2.24 (s, 3H), 2.85 (q, 2H), 3.13 (s, 3H), 3.68 (s, 3H), 3.93 (s, 3H), 7.45 (d, 1H), 7.68 (s, 1H), 7.91 (d, 1H). 2 1.31 (t, 3H), 1.41 (t, 3H), 2.27 (s, 3H), 2.88 (q, 2H), 3.21 (s, 3H), 3.96 (s, 3H), 4.03 (q, 2H), 7.48 (d, 1H), 7.70 (s, 1H), 7.93 (d, 1H). 3 2.26 (s, 3H), 2.36 (s, 3H), 3.16 (s, 3H), 3.70 (s, 3H), 3.97 (s, 3H), 7.46 (d, 1H, J = 8.4 Hz), 7.73 (s, 1H), 7.94 (d, 1H, 8.4 Hz). 4 1.42 (t, 3H, J = 7.3 Hz), 2.27 (s, 3H), 2.37 (s, 3H), 3.17 (s, 3H), 3.97 (s, 3H), 4.01 (q, 2H, J = 7.3 Hz), 7.47 (d, 1H, J = 7.8 Hz), 7.74 (s, 1H), 7.94 (d, 1H, J = 7.8 Hz). 16 1.33 (t, 3H, J = 7.3 Hz), 1.42 (t, 3H, J = 7.3 Hz), 2.30 (s, 3H), 2.89 (q, 2H, J = 7.3 Hz), 3.27 (s, 3H), 3.45 (s, 3H), 3.79 (m, 2H), 4.01 (q, 2H, J = 7.3 Hz), 7.21 (d, 1H, J = 7.8 Hz), 7.65 (s, 1H), 7.86 (d, 1H, J = 7.8 Hz). 27 1.32 (t, 3H, J = 7.4 Hz), 2.89 (q, 2H, J = 7.4 Hz), 3.18 (s, 3H), 3.71 (s, 3H), 3.99 (s, 3H), 7.52 (d, 1H, J = 8.2 Hz), 7.75 (s, 1H), 8.01 (d, 1H, J = 8.4 Hz). 29 2.38 (s, 3H), 3.18 (s, 3H), 3.71 (s, 3H), 3.99 (s, 3H), 7.52 (d, 1H, J = 8.4 Hz), 7.76 (s, 1H), 8.02 (d, 1H, J = 8.0 Hz). 31 1.32 (t, 3H, J = 7.4 Hz), 2.59 (s, 3H), 2.89 (q, 2H, J = 7.4 Hz), 3.16 (s, 3H), 3.71 (s, 3H), 7.52 (d, 1H, J = 7.8 Hz), 7.78 (s, 1H), 8.04 (d, 1H, J = 7.8 Hz). 35 1.32 (t, 3H, J = 7.3 Hz), 2.27 (s, 3H), 2.89 (q, 2H, J = 7.3 Hz), 3.23 (s, 3H), 3.72 (s, 3H), 3.95 (s, 3H), 7.19 (d, 1H, J = 7.6 Hz), 7.67 (s, 1H), 7.85 (d, 1H, J = 7.6 Hz) 36 1.33 (t, 3H, J = 7.2 Hz), 1.47 (t, 3H, J = 7.2 Hz), 2.26 (s, 3H), 2.88 (q, 2H, J = 7.2 Hz), 3.25 (s, 3H), 3.72 (s, 3H), 4.12 (q, 2H, J = 7.2 Hz), 7.18 (d, 1H, J = 7.9 Hz), 7.69 (s, 1H), 7.85 (d, 1H, J = 7.9 Hz). 37 1.33 (m, 9H), 2.24 (s, 3H), 2.91 (q, 2H, J = 7.5 Hz), 3.21 (s, 3H), 3.72 (s, 3H), 4.82 (qq, 1H, J = 6.0, 6.0 Hz), 7.15 (d, 1H, J = 8.0 Hz), 7.63 (s, 1H), 7.90 (d, 1H, J = 8.0 Hz). 38 1.33 (t, 3H, J = 7.4 Hz), 2.33 (s, 3H), 2.89 (q, 2H, J = 7.4 Hz), 3.21 (s, 3H), 3.72 (s, 3H), 6.75 (t, 1H, J = 75.2 Hz), 7.35 (d, 1H, J = 8.4 Hz), 7.67 (s, 1H), 7.96 (d, 1H, J = 8.4 Hz). 39 1.32 (t, 3H, J = 7.5 Hz), 2.25 (s, 3H), 2.89 (q, 2H, J = 7.5 Hz), 3.18 (s, 3H), 3.3 (br s, 2H), 3.72 (s, 3H), 4.57 (t, 2H, J = 10 Hz), 7.50 (d, 1H, J = 8.4 Hz), 7.70 (s, 1H), 8.04 (d, 1H, J = 8.4 Hz). 40 2.15 (s, 3H), 2.37 (s, 3H), 3.18 (s, 3H), 3.3 (br s, 2H), 3.72 (s, 3H), 4.57 (t, 2H, J = 10.2 Hz), 7.49 (d, 1H, J = 8.0 Hz), 7.73 (s, 1H), 8.04 (d, 1H, J = 8.0 Hz). 42 1.31 (t, 3H, J = 7.4 Hz), 2.87 (q, 2H, J = 7.4 Hz), 3.25 (s, 3H), 3.49 (s, 3H), 3.70 (s, 3H), 5.09 (s, 2H), 7.42 (d, 1H, J = 8.0 Hz), 7.70 (s, 1H), 8.11 (d, 1H, J = 8.0 Hz). 55 1.33 (t, 3H, J = 7.4 Hz), 2.29 (s, 3H), 2.89 (q, 2H, J = 7.4 Hz), 3.28 (s, 3H), 3.45 (s, 3H), 3.72 (s, 3H), 3.79 (m, 2H), 4.23 (m, 2H), 7.20 (d, 1H, J = 8.0 Hz), 7.66 (s, 1H), 7.86 (d, 1H, J = 8.0 Hz). 58 1.33 (t, 3H, J = 7.4 Hz), 1.42 (t, 3H, J = 7.4 Hz), 1.47 (t, 3H, J = 6.8 Hz), 2.26 (s, 3H), 2.89 (q, 2H, J = 7.4 Hz), 3.25 (s, 3H), 4.02 (q, 2H, J = 7.4 Hz), 4.12 (q, 2H, J = 6.8 Hz), 7.19 (d, 1H, J = 8.0 Hz), 7.66 (s, 1H), 7.85 (d, 1H, J = 8.0 Hz). 59 1.32 (t, 3H, J = 7.6 Hz), 1.40 (t, 3H, J = 7.2 Hz), 1.43 (t, 3H, J = 7.2 Hz), 2.90 (q, 2H, J = 7.6 Hz), 4.01 (q, 2H, J = 7.3 Hz), 4.47 (q, 2H, J = 7.2 Hz), 7.52 (d, 1H, J = 8.4 Hz), 7.74 (s, 1H), 8.01 (d, 1H, J = 8.4 Hz). 60 1.00 (t, 3H, J = 7.6 Hz), 1.33 (t, 3H, J = 7.4 Hz), 1.43 (t, 3H, J = 7.2 Hz), 1.80 (qt, 2H, J = 6.9, 6.9 Hz), 2.90 (q, 2H, J = 7.3 Hz), 3.19 (s, 3H), 4.01 (q, 2H, J = 7.3 Hz), 4.37 (t, 2H, J = 6.8 Hz), 7.52 (d, 1H, J = 8.4 Hz), 7.74 (s, 1H), 8.01 (d, 1H, J = 8.4 Hz). 61 1.31 (t, 3H, J = 7.2 Hz), 1.39 (t, 3H, J = 7.2 Hz), 1.42 (t, 3H, J = 7.4 Hz), 2.29 (s, 3H), 2.89 (d, 2H, J = 7.4 Hz), 3.17 (s, 3H), 4.01 (q, 2H, J = 7.2 Hz), 4.44 (d, 2H, J = 7.2 Hz), 7.47 (d, 1H, J = 7.6 Hz), 7.71 (s, 1H), 7.93 (d, 7.6 Hz). 62 1.39 (t, 3H, J = 7.4 Hz), 1.42 (t, 3H, J = 7.4 Hz), 2.28 (s, 3H), 2.37 (s, 3H), 3.17 (s, 3H), 4.01 (q, 2H, J = 7.4 Hz), 4.44 (q, 2H, J = 7.1 Hz), 7.47 (d, 1H, J = 8.4 Hz), 7.74 (s, 1H), 7.94 (d, 1H, 8.4 Hz). 63 1.31 (t, 3H, J = 7.4 Hz), 2.37 (s, 3H), 2.87 (q, 2H, J = 7.4 Hz), 3.19 (s, 3H), 3.48 (s, 3H), 3.71 (s, 3H), 4.93 (s, 2H), 7.37 (d, 1H, J = 8.2 Hz), 7.64 (s, 1H), 8.03 (d, 1H, J = 8.2 Hz) 64 1.35 (t, 3H, J = 7.5 Hz), 2.24 (s, 3H), 2.91 (q, 2H, J = 7.5 Hz), 3.15 (s, 3H), 3.734 (s, 3H), 3.736 (s, 3H), 4.40 (s, 2H), 7.39 (d, 1H, J = 8.1 Hz), 7.65 (s, 1H), 8.05 (d, 1H, J = 8.1 Hz). 65 1.31 (t, 3H, J = 7.2 Hz), 1.34 (t, 3H, J = 7.4 Hz), 2.27 (s, 3H), 2.89 (q, 2H, J = 7.3 Hz), 3.35 (s, 3H), 3.19 (s, 3H), 4.29 (q, 2H, J = 7.2 Hz), 4.65 (s, 2H), 7.26 (d, 1H, J = 8.0 Hz), 7.67 (s, 1H), 7.87 (d, 1H, J = 8.0 Hz) 66 1.06 (t, 3H, J = 7.6 Hz), 1.32 (t, 3H, J = 7.6 Hz), 1.89 (qt, 2H, J = 6.9, 7.1 Hz), 2.25 (s, 3H), 2.32 (q, 2H, J = 7.3 Hz), 3.33 (s, 3H), 3.71 (s, 3H), 4.03 (t, 2H, J = 6.7 Hz), 7.17 (d, 1H, J = 8.0 Hz), 7.66 (s, 1H), 7.85 (d, 1H, J = 8.0 Hz). 67 1.06 (t, 3H, J = 7.2 Hz), 1.34 (t, 3H, J = 7.2 Hz), 1.42 (t, 3H, J = 7.0 Hz), 1.89 (qt, 2H, J = 6.9, 6.9 Hz), 2.26 (s, 3H), 2.89 (q, 2H, J = 7.2 Hz), 3.24 (s, 3H), 3.9-4.0 (m, 4H), 7.19 (d, 1H, J = 8.0 Hz), 7.66 (s, 1H), 7.86 (d, 1H, J = 8.0 Hz). 68 1.31 (t, 3H, J = 7.2 Hz), 1.43 (t, 3H, J = 7.4 Hz), 2.87 (q, 2H, J = 7.4 Hz), 3.28 (s, 3H), 3.99 (q, 2H, J = 7.2 Hz), 7.58 (d, 1H, J = 7.6 Hz), 7.69 (s, 1H), 7.93 (d, 1H, J = 7.6 Hz), 8.37 (br s, 1H). 69 1.30 (t, 3H, J = 7.2 Hz), 2.38 (s, 3H), 2.86 (q, 2H, J = 7.2 Hz), 3.16 (s, 3H), 3.72 (s, 3H), 4.00 (q, 2H, J = 8.8 Hz), 5.21 (s, 1H), 7.42 (d, 1H, J = 8.2 Hz), 7.67 (s, 1H), 8.05 (d, 1H, J = 8.2 Hz). 70 1.32 (t, 3H, J = 7.6 Hz), 2.87 (q, 2H, J = 7.6 Hz), 3.22 (s, 3H), 3.71 (s, 3H), 4.02 (q, 2H, J = 8.8 Hz), 5.35 (s, 2H), 7.48 (d, 1H, J = 8.4 Hz), 7.72 (s, 1H), 8.14 (d, 1H, J = 8.4 Hz). 71 1.27 (t, 3H, J = 7.2 Hz), 1.37 (t, 3H, J = 7.2 Hz), 2.33 (s, 3H), 2.83 (q, 2H, J = 7.2 Hz), 3.25 (s, 3H), 3.96 (q, 2H, J = 7.2 Hz), 7.30 (d, 1H, J = 7.8 Hz), 7.65 (s, 1H), 8.03 (d, 1H, J = 7.8 Hz). 72 1.33 (t, 3H, J = 7.2 Hz), 2.49 (s, 3H), 2.90 (q, 2H, J = 7.2 Hz), 3.01 (s, 3H), 3.29 (s, 3H), 3.71 (s, 3H), 7.44 (d, 1H, J = 8.0 Hz), 7.63 (s, 1H), 8.02 (d, 1H, J = 8.0 Hz). 73 1.24 (t, 3H, J = 6.8 Hz), 1.31 (t, 3H, J = 7.2 Hz), 2.37 (s, 3H), 2.86 (q, 2H, J = 7.2 Hz), 3.29 (s, 3H), 3.67 (q, 2H, J = 6.8 Hz), 3.71 (s, 3H), 4.97 (s, 2H), 7.37 (d, 1H, J = 8.0 Hz), 7.65 (s, 1H), 8.03 (d, 1H, J = 8.0 Hz). 74 2.36 (s, 3H), 3.26 (s, 3H), 3.49 (s, 3H), 3.71 (s, 3H), 5.09 (s, 2H), 7.42 (d, 1H, J = 8.0 Hz), 7.71 (s, 1H), 8.12 (d, 1H, J = 8.0 Hz). 75 1.33 (t, 3H, J = 7.2 Hz), 2.33 (s, 3H), 2.88 (q, 2H, J = 7.2 Hz), 3.15 (s, 3H), 3.33 (s, 1H), 3.41 (t, 2H, J = 7.4 Hz), 3.63 (t, 2H, J = 7.4 Hz), 3.71 (s, 3H), 7.27 (d, 1H, J = 8.4 Hz), 7.64 (s, 1H), 8.00 (d, 1H, J = 8.4 Hz). 76 1.32 (t, 3H, J = 7.2 Hz), 2.38 (s, 3H), 2.88 (q, 2H, J = 7.2 Hz), 3.24 (s, 3H), 3.33 (s, 3H), 3.56 (m, 2H), 3.71 (s, 3H), 3.76 (m, 2H), 5.04 (s, 2H), 7.37 (d, 1H, J = 7.6 Hz), 7.64 (s, 1H), 8.03 (d, 1H, J = 7.6 Hz). 77 1.23 (t, 3H, J = 6.8 Hz), 1.33 (t, 3H, J = 7.2 Hz), 2.30 (s, 3H), 2.88 (q, 2H, J = 7.2 Hz), 3.28 (s, 3H), 3.60 (q, 2H, J = 6.8 Hz), 3.71 (s, 3H), 3.82 (m, 2H), 4.24 (m, 2H), 7.18 (d, 1H, J = 7.8 Hz), 7.66 (s, 1H), 7.85 (d, 1H, J = 7.8 Hz). 78 1.34 (t, 3H, J = 7.2 Hz), 2.31 (s, 3H), 2.89 (q, 2H, J = 7.2 Hz), 3.26 (s, 3H), 3.72 (s, 3H), 3.91 (t, 2H, J = 5.2 Hz), 4.33 (t, 2H, J = 5.2 Hz), 7.23 (d, 1H, J = 8.0 Hz), 7.67 (s, 1H), 7.87 (d, 1H, J = 8.0 Hz). 79 1.35 (t, 3H, J = 7.2 Hz), 2.30 (s, 3H), 2.89 (q, 2H, J = 7.2 Hz), 3.26 (s, 3H), 3.72 (s, 3H), 4.49 (q, 2H, J = 8.4 Hz), 7.30 (d, 1H, J = 8.0 Hz), 7.67 (s, 1H), 7.90 (d, 1H, J = 8.0 Hz). 81 1.34 (t, 3H, J = 7.2 Hz), 2.19 (s, 3H), 2.29 (s, 3H), 2.89 (q, 2H, J = 7.2 Hz), 2.96 (t, 2H, J = 6.6 Hz), 3.27 (s, 3H), 3.72 (s, 3H), 4.23 (t, 2H, J = 6.6 Hz), 7.20 (d, 1H, J = 8.4 Hz), 7.67 (s, 1H), 7.87 (d, 1H, J = 8.4 Hz). 82 1.34 (t, 3H, J = 7.4 Hz), 2.61 (s, 3H), 2.90 (q, 2H, J = 7.5 Hz), 3.32 (s, 3H), 3.74 (s, 3H), 7.67 (d, 1H, J = 8.1 Hz), 7.72 (s, 1H), 8.12 (d, 1H, J = 8.1 Hz). 83 1.34 (t, 3H, J = 7.4 Hz), 2.44 (s, 3H), 2.91 (q, 2H, J = 7.3 Hz), 3.22 (s, 3H), 3.74 (s, 3H), 4.44 (s, 2H), 7.48 (d, 1H, J = 8.1 Hz), 7.69 (s, 1H), 8.10 (d, 1H, J = 8.1 Hz). 84 0.99 (t, 3H, J = 7.4 Hz), 1.65 (qt, 2H, J = 7.4, 7.4 Hz), 2.27 (s, 3H), 2.85 (t, 2H, J = 7.2 Hz), 3.16 (s, 3H), 3.71 (s, 3H), 3.97 (s, 3H), 7.47 (d, 1H, J = 8.0 Hz), 7.69 (s, 1H), 7.94 (d, 1H, J = 8.0 Hz) 85 0.99 (t, 3H, J = 7.4 Hz), 1.42 (t, 3H, J = 7.2 Hz), 1.67 (qt, 2H, J = 7.4, 7.4 Hz), 2.28 (s, 3H), 2.86 (t, 2H, J = 7.4 Hz), 3.16 (s, 3H), 3.96 (s, 3H), 4.02 (quartet, 2H, J = 7.3 Hz), 7.44 (d, 1H, J = 8.0 Hz), 7.69 (s, 1H), 7.94 (d, 1H, J = 8.0 Hz) 86 1.34 (d, 6H, J = 4.8 Hz), 2.28 (s, 3H), 3.16 (s, 3H), 3.50 (quintet, 1H, J = 6.8 Hz), 3.71 (s, 3H), 3.97 (s, 3H), 7.48 (d, 1H, J = 8.0 Hz), 7.69 (s, 1H), 7.94 (d, 1H, J = 8.0 Hz) 87 1.34 (d, 6H, J = 4.8 Hz), 1.42 (t, 3H, J = 7.4 Hz), 2.28 (s, 3H), 3.16 (s, 3H), 3.51 (quintet, 1H, J = 6.9 Hz), 3.97 (s, 3H), 4.02 (quartet, 2H, J = 7.3 Hz), 7.48 (d, 1H, J = 8.0 Hz), 7.69 (s, 1H), 7.94 (d, 1H, J = 8.0 Hz) 88 0.98 (t, 3H, J = 7.4 Hz), 1.36 (d, 6H, J = 6.8 Hz), 1.61-1.70 (m, 2H), 2.73 (s, 3H), 3.16 (s, 3H), 3.36 (qt, 1H, J = 6.8, 6.8 Hz), 3.71 (s, 3H), 3.96 (s, 3H), 7.48 (d, 1H, J = 7.6 Hz), 7.65 (s, 1H), 7.94 (d, 1H, J = 7.6 Hz) 89 0.98 (t, 3H), 1.33 (d, 3H), 1.42 (t, 3H), 1.61-1.69 (m, 2H), 2.28 (s, 3H), 3.16 (s, 3H), 3.35 (m, 1H), 3.96 (s, 3H), 4.04 (q, 2H), 7.49 (d, 1H), 7.64 (s, 1H), 7.93 (d, 1H). 90 1.47 (s, 9H), 2.29 (s, 3H), 3.17 (s, 3H), 3.71 (s, 3H), 3.96 (s, 3H), 7.48 (d, 1H, J = 8.0 Hz), 7.67 (s, 1H), 7.94 (d, 1H, J = 8.0 Hz) 91 1.42 (t, 3H, J = 7.2 Hz), 1.47 (s, 9H), 2.29 (s, 3H), 3.17 (s, 3H), 3.96 (s, 3H), 4.02 (quartet, 2H, J = 7.3 Hz), 7.49 (d, 1H, J = 8.0 Hz), 7.67 (s, 1H), 7.94 (d, 1H, J = 8.0 Hz) 92 2.29 (s, 3H), 3.14 (s, 3H), 3.68 (s, 3H), 3.98 (s, 3H), 4.130 (s, 2H), 7.26-7.33 (m, 5H), 7.47 (d, 1H, J = 8.0 Hz), 7.71 (s, 1H), 7.93 (d, 1H, J = 8.0 Hz) 93 1.38 (t, 3H, J = 7.2 Hz), 2.29 (s, 3H), 3.15 (s, 3H), 3.95-4.00 (m, 5H), 4.10 (s, 2H), 7.25-7.34 (m, 5H), 7.43 (d, 1H, J = 8.0 Hz), 7.71 (s, 1H), 7.93 (d, 1H, J = 8.0 Hz) 95 1.31 (t, 3H, J = 7.4 Hz), 1.40 (t, 3H, J = 7.4 Hz), 2.88 (q, 2H, J = 7.4 Hz), 3.17 (s, 3H), 3.97 (s, 3H), 3.98 (q, 2H, J = 7.4 Hz), 7.52 (d, 1H, J = 8.0 Hz), 7.73 (s, 1H), 7.97 (d, 1H, J = 8.0 Hz). 97 1.42 (t, 3H, J = 7.4 Hz), 2.38 (s, 3H), 3.18 (s, 3H), 4.00 (s, 3H), 4.03 (q, 2H, J = 7.4 Hz), 7.52 (d, 1H, J = 8.0 Hz), 7.75 (s, 1H), 8.00 (d, 1H, J = 8.0 Hz). 99 1.41 (t, 3H, J = 7.4 Hz), 2.27 (s, 3H), 3.16 (s, 3H), 3.53 (d, 2H, J = 7.6 Hz), 3.98 (s, 3H), 4.02 (q, 2H, J = 7.4 Hz), 5.19 (d, 1H, 10.9 Hz), 5.30 (d, 1H, J = 18.5 Hz), 5.8-5.9 (m, 1H), 7.48 (d, 1H, J = 8.0 Hz), 7.71 (s, 1H), 7.94 (d, 1H, J = 8.0 Hz). 101 1.37 (t, 3H, J = 7.4 Hz), 1.75 (s, 3H), 2.23 (s, 3H), 3.11 (s, 3H), 3.50 (s, 2H), 3.74 (s, 3H), 3.93 (q, 2H, J = 7.4 Hz), 4.86 (s, 1H), 4.96 (s, 1H), 7.44 (d, 1H, J = 8.0 Hz), 7.63 (s, 1H), 7.89 (d, 1H, J = 8.0 Hz). 189 1.27 (d, 3H, J = 6.4 Hz), 1.33 (t, 3H, J = 7.8 Hz), 2.29 (s, 3H), 2.89 (q, 2H, J = 7.8 Hz), 3.27 (s, 3H), 3.45 (s, 3H), 3.71 (s, 3H), 3.80 (m, 1H), 4.07 (m, 2H), 7.19 (d, 1H, J = 8.0 Hz), 7.65 (s, 1H), 7.86 (d, 1H, J = 8.0 Hz). 207 1.37 (d, 6H, J = 7.0 Hz), 2.29 (s, 3H), 3.27 (s, 3H), 3.45 (s, 3H), 3.50 (tt, 1H, J = 7.0, 7.0 Hz), 3.71 (s, 3H), 3.79 (m, 2H), 4.24 (m, 2H), 7.20 (d, 1H, J = 7.6 Hz), 7.66 (s, 1H), 7.86 (d, 1H, J = 7.6 Hz). 208 1.36 (d, 6H, J = 6.8 Hz), 1.42 (t, 3H, J = 7.2 Hz), 2.29 (s, 3H), 3.27 (s, 3H), 3.44 (s, 3H), 3.51 (tt, 1H, J = 6.8, 6.8 Hz), 3.79 (m, 2H), 4.00 (q, 2H, J = 7.2 Hz), 4.23 (m, 2H), 7.20 (d, 1H, J = 8.2 Hz), 7.64 (s, 1H), 7.85 (d, 1H, J = 8.2 Hz). 209 1.33 (t, 3H, J = 7.4 Hz), 2.28 (s, 3H), 2.88 (q, 2H, J = 7.4 Hz), 3.27 (s, 3H), 3.47 (s, 6H), 3.71 (s, 3H), 4.09 (d, 2H, J = 5.4 Hz), 4.83 (t, 1H, J = 5.4 Hz), 7.20 (d, 1H, J = 8.2 Hz), 7.66 (s, 1H), 7.86 (d, 1H, J = 8.2 Hz). 210 1.34 (t, 3H, J = 7.5 Hz), 2.39 (s, 6H), 2.89 (q, 2H, J = 7.5 Hz), 3.26 (s, 3H), 3.63 (s, 2H), 3.73 (s, 3H), 4.21 (s, 2H), 7.38 (d, 1H, J = 8.1 Hz), 7.67 (s, 1H), 8.08 (d, 1H, J = 8.1 Hz). 211 1.33 (t, 3H, J = 7.6 Hz), 1.69 (m, 2H), 1.93 (m, 2H), 2.30 (s, 3H), 2.89 (q, 2H, J = 7.6 Hz), 3.28 (s, 3H), 3.17 (s, 3H), 3.85 (dt, 1H, J = 8.4, 6.8 Hz), 3.94 (dt, 1H, J = 8.4, 6.8 Hz), 4.07 (m, 2H), 4.37 (m, 1H), 7.20 (d, 1H, J = 7.6 Hz), 7.66 (s, 1H), 7.86 (d, 1H, J = 7.6 Hz). 212 1.32 (t, 3H, J = 7.4 Hz), 2.32 (s, 3H), 2.48 (s, 3H), 2.88 (q, 2H, J = 7.2 Hz), 3.70 (s, 3H), 7.11 (d, 1H, J = 8.4 Hz), 7.16 (d, 1H, J = 8.4 Hz), 7.67 (s, 1H). 213 1.33 (t, 3H, J = 7.6 Hz), 2.50 (s, 3H), 2.90 (q, 2H, J = 7.6 Hz), 3.71 (s, 3H), 7.06 (d, 1H, J = 8.4 Hz), 7.24 (d, 1H, J = 8.4 Hz), 7.68 (s, 1H) 214 1.32 (t, 3H, J = 7.4 Hz), 2.88 (q, 2H, J = 7.4 Hz), 3.26 (s, 3H), 3.71 (s, 3H), 4.10 (s, 3H), 7.21 (d, 1H, J = 8.0 Hz), 7.73 (s, 1H), 7.92 (d, 1H, J = 8.0 Hz). 215 1.33 (t, 3H, J = 7.4 Hz), 1.5-1.9 (m, 6H), 2.29 (s, 3H), 2.89 (q, 2H, J = 7.4 Hz), 3.27 (s, 3H), 3.52 (m, 1H), 3.71 (s, 3H), 3.81 (m, 1H), 3.9-4.1 (m, 3H), 7.18 (d, 1H, J = 8.4 Hz), 7.65 (s, 1H), 7.85 (d, 1H, J = 8.4 Hz). 216 1.33 (t, 3H, J = 7.2 Hz), 2.87 (q, 2H, J = 7.2 Hz), 3.31 (s, 3H), 3.46 (s, 3H), 3.70 (s, 3H), 3.83 (m, 2H), 4.44 (m, 2H), 7.22 (d, 1H, J = 8.0 Hz), 7.72 (s, 1H), 7.94 (d, 1H, J = 8.0 Hz). 217 1.34 (t, 3H, J = 7.2 Hz), 2.12 (m, 1H), 2.40 (m, 1H), 2.90 (q, 2H, J = 7.2 Hz), 3.21 (s, 3H), 3.72 (s, 3H), 3.8-3.9 (m, 2H), 4.1-4.2 (m, 2H), 5.16 (m, 1H), 7.19 (d, 1H, J = 8.4 Hz), 7.67 (s, 1H), 7.93 (d, 1H, J = 8.4 Hz). 218 1.33 (t, 3H, J = 7.4 Hz), 2.13 (tt, 2H, J = 6.4, 6.4 Hz), 2.26 (s, 3H), 2.88 (q, 2H, J = 7.4 Hz), 3.23 (s, 3H), 3.35 (s, 3H), 3.59 (t, 2H, J = 6.4 Hz), 3.71 (s, 3H), 4.16 (t, 2H, J = 6.4 Hz), 7.18 (d, 1H, J = 8.0 Hz), 7.67 (s, 1H), 7.85 (d, 1H, J = 8.0 Hz). 219 0.99 (t, 3H, J = 7.4 Hz), 1.68 (qt, 2H, J = 7.4, 7.4 Hz), 2.30 (s, 3H), 2.86 (t, 3H, J = 7.4 Hz), 3.27 (s, 3H), 3.45 (s, 3H), 3.71 (s, 3H), 3.79 (m, 2H), 4.23 (m, 2H), 7.19 (d, 1H, J = 8.0 Hz), 7.64 (s, 1H), 7.86 (d, 1H, J = 8.0 Hz). 220 0.98 (t, 3H, J = 7.4 Hz), 1.36 (d, 3H, J = 7.4 Hz), 1.43 (t, 3H, J = 7.4 Hz), 1.6-1.7 (m, 2H), 3.15 (s, 3H), 3.3-3.4 (m, 1H), 4.00 (s, 3H), 4.0-4.1 (m, 2H), 7.54 (d, 1H, J = 8.2 Hz), 7.72 (s, 1H), 8.01 (d, 1H, J = 8.2 Hz). 221 1.33 (t, 3H, J = 7.4 Hz), 1.42 (t, 3H, J = 7.4 Hz), 2.3-2.3 (m, 2H), 2.88 (q, 2H, J = 7.4 Hz), 3.28 (s, 3H), 3.8-3.9 (m, 2H), 3.9-4.1 (m, 4H), 4.43 (t, 2H, J = 5.4 Hz), 5.14 (t, 1H, J = 5.4 Hz), 7.22 (d, 1H, J = 8.2 Hz), 7.72 (s, 1H), 7.92 (d, 1H, J = 8.2 Hz). 222 1.33 (t, 3H, J = 7.4 Hz), 2.33 (s, 3H), 2.62 (t, 1H, J = 2.4 Hz), 3.28 (s, 3H), 3.72 (s, 3H), 4.76 (d, 2H, J = 2.4 Hz), 7.23 (d, 1H, J = 7.2 Hz), 7.66 (s, 1H), 7.86 (d, 1H, J = 7.2 Hz). 223 1.32 (t, 3H, J = 7.2 Hz), 2.07 (m, 2H), 2.37 (s, 3H), 2.87 (q, 2H, J = 7.2 Hz), 3.19 (s, 3H), 3.71 (s, 3H), 3.75-3.95 (m, 4H), 4.31 (m, 1H), 4.97 (d, 2H, J = 10.4 Hz), 5.02 (d, 2H, J = 10.4 Hz), 7.38 (d, 1H, J = 8.0 Hz), 7.65 (s, 1H), 8.03 (d, 1H, J = 8.0 Hz). 224 1.28 (t, 3H, J = 7.6 Hz), 2.48 (3H, s), 2.81 (q, 2H, J = 7.6 Hz), 3.41 (s, 3H), 3.65 (s, 3H), 7.38 (d, 1H, J = 8.4 Hz), 7.70 (s, 1H), 8.12 (d, 2H, J = 8.4 Hz) 225 0.87 (t, 3H, J = 6.9 Hz), 1.25-1.57 (m, 10H), 1.32 (t, 3H, J = 7.6 Hz), 2.29 (s, 3H), 2.87 (q, 2H, J = 7.6 Hz), 3.01 (m, 1H), 3.09 (s, 3H), 3.71 (s, 3H), 7.23 (d, 1H, J = 7.6 Hz), 7.66 (s, 1H), 7.97 (d, 1H, J = 7.6 Hz). 226 1.32 (t, 3H, J = 7.6 Hz), 1.97 (m, 2H), 2.31 (s, 3H), 2.86 (q, 2H, J = 7.6 Hz), 3.11 (s, 3H), 3.12 (m, 2H), 3.36 (s, 3H), 3.50 (t, 2H, J = 6.2 Hz), 3.70 (s, 3H), 7.24 (d, 1H, J = 8.4 Hz), 7.67 (s, 1H), 7.97 (d, 1H, J = 8.4 Hz). 227 1.32 (t, 3H, J = 7.4 Hz), 1.42 (t, 3H, J = 7.4 Hz), 2.88 (q, 2H, J = 7.4 Hz), 3.31 (s, 3H), 3.9-4.1 (m, 6H), 4.29 (d, 2H, J = 5.4 Hz), 5.47 (t, 1H, J = 5.4 Hz), 7.25 (d, 1H, J = 8.2 Hz), 7.74 (s, 1H), 7.94 (d, 1H, J = 8.2 Hz). 228 1.31-1.44 (m, 6H), 2.33 (s, 3H), 2.96-3.05 (m, 4H), 3.14 (s, 3H), 3.74 (s, 3H), 4.37 (s, 2H), 5.21 (s, 2H), 7.50 (d, 1H, J = 8.1 Hz), 7.62 (s, 1H), 8.10 (d, 1H, J = 8.1 Hz). 229 1.34 (t, 3H, J = 7.5 Hz), 2.30 (s, 3H), 2.89 (q, 2H, J = 7.5 Hz), 3.06 (s, 3H), 3.74 (s, 3H), 5.68 (d, 1H, J = 17.1 Hz), 7.47 (d, 1H, J = 8.1 Hz), 7.70 (s, 1H), 8.00 (d, 1H, J = 17.1 Hz), 8.05 (d, 1H, J = 8.1 Hz). 230 1.36 (t, 3H, J = 7.5 Hz), 2.38 (s, 3H), 2.76 (t, 2H, J = 7.8 Hz), 2.92 (q, 2H, J = 7.5 Hz), 3.14 (s, 3H), 3.43 (q, 2H, J = 7.8 Hz), 3.74 (s, 3H), 7.37 (d, 1H, J = 8.1 Hz), 7.66 (s, 1H), 8.01 (d, 1H, J = 8.1 Hz). 231 1.36 (t, 3H, J = 7.5 Hz), 2.49 (s, 3H), 2.92 (q, 2H, J = 7.5 Hz), 3.22 (s, 3H), 3.74 (s, 3H), 4.86 (s, 2H), 7.46 (d, 1H, J = 8.1 Hz), 7.66 (s, 1H), 8.03 (d, 1H, J = 8.1 Hz). 232 1.37 (t, 3H, J = 7.5 Hz), 2.40 (s, 3H), 2.96 (q, 2H, J = 7.5 Hz), 3.19 (s, 3H), 3.74 (s, 3H), 4.63 (s, 2H), 7.34 (br, 1H), 7.40 (d, 1H, J = 8.1 Hz), 7.49 (br, 1H), 7.62 (s, 1H), 8.06 (d, 1H, J = 8.1 Hz). 233 2.29 (s, 3H), 2.38 (s, 3H), 3.28 (s, 3H, 3.45 (s, 3H), 3.71 (s, 3H), 3.79 (m, 2H), 4.23 (m, 2H), 7.19 (d, 1H, J = 7.6 Hz), 7.66 (s, 1H), 7.86 (d, 1H, 7.6 Hz). 234 1.42 (t, 3H, J = 7.4 Hz), 2.30 (s, 3H), 2.38 (s, 3H), 3.28 (s, 3H), 3.45 (s, 3H), 3.79 (m, 2H), 4.01 (q, 2H, J = 7.6 Hz), 4.23 (m, 2H), 7.22 (d, 1H, J = 8.4 Hz), 7.65 (s, 1H), 7.86 (d, 1H, J = 8.4 Hz). 235 0.99 (t, 3H, J = 7.4 Hz), 1.42 (t, 3H, J = 7.4 Hz), 1.68 (qt, 2H, J = 7.4, 7.4 Hz), 2.29 (s, 3H), 2.86 (t, 2H, J = 7.4 Hz), 3.27 (s, 3H), 3.45 (s, 3H), 3.79 (m, 2H), 4.01 (q, 2H, J = 7.4 Hz), 4.23 (m, 2H), 7.20 (d, 1H, J = 8.4 Hz), 7.63 (s, 1H), 7.85 (d, 1H, J = 8.4 Hz). 236 1.23 (d, 3H, J = 7.4 Hz), 1.37 (t, 3H, J = 7.4 Hz), 2.29 (s, 3H), 2.90-2.96 (m, 2H), 3.23 (s, 3H), 3.35 (s, 3H), 3.51-3.53 (m, 1H), 3.70-3.75 (m, 1H), 3.73 (s, 3H), 4.85-4.90 (m, 1H), 7.18 (d, 1H, J = 8.2 Hz), 7.60 (s, 1H), 7.89 (d, 1H, J = 8.2 Hz). 238 1.33 (t, 3H, J = 7.1 Hz), 2.37 (s, 3H), 2.90 (q, 2H, J = 7.1 Hz), 3.19 (s, 3H), 3.66 (d, 2H, J = 6.0 Hz), 3.71 (s, 3H), 3.78-3.86 (m, 2H), 3.95-4.00 (m, 2H), 5.17 (t, 1H, J = 6.0 Hz), 7.31 (d, 1H, J = 9.4 Hz), 7.66 (s, 1H), 8.01 (d, 1H, J = 9.4 Hz). 239 1.01 (t, 3H, J = 6.8 Hz), 1.39 (d, 3H, J = 7.4 Hz), 1.61-1.75 (m, 2H), 2.32 (s, 3H), 3.30 (s, 3H), 3.39 (m, 1H), 3.48 (s, 3H), 3.74 (s, 3H), 3.77-3.83 (m, 2H), 4.25-4.27 (m, 2H), 7.23 (d, 1H, J = 8.2 Hz), 7.66 (s, 1H), 7.89 (d, 1H, J = 8.2 Hz). 240 1.24 (d, 6H), J = 6.4 Hz), 1.31 (t, 3H, J = 7.2 Hz), 1.42 (t, 3H, J = 7.2 Hz), 2.37 (s, 3H), 2.88 (q, 2H, J = 7.2 Hz), 3.23 (s, 3H), 3.80 (m, 1H), 4.01 (q, 2H, J = 7.2 Hz), 4.97 (s, 2H), 7.38 (d, 1H, J = 8.0 Hz), 7.64 (s, 1H), 8.02 (d, 1H, J = 8.0 Hz). 241 1.47 (s, 9H), 2.29 (s, 3H), 3.23 (s, 3H), 3.45 (s, 3H), 3.67 (s, 3H), 3.79 (m, 2H), 4.24 (m, 2H), 7.18 (d, 1H, J = 8.0 Hz), 7.68 (s, 1H), 7.85 (d, 1H, J = 8.0 Hz). 242 2.29 (s, 3H), 3.27 (s, 3H), 3.44 (s, 3H), 3.72 (s, 2H), 3.73 (s, 3H), 3.78 (s, 3H), 3.79 (m, 2H), 4.23 (m, 2H), 7.20 (d, 1H, J = 8.4 Hz), 7.61 (s, 1H), 7.87 (d, 1H, J = 8.4 Hz).

TABLE 3 (II-x)

No. R¹ R² R⁴ R^(5-x) R⁶ 2-1 Me H Me CO₂Me SO₂Me 2-2 Et H Me CO₂Me SO₂Me 2-3 Et H Me CO₂(i-Pr) SO₂Me 2-4 Me H Cl CO₂Et SO₂Me 2-5 Et H Me CO₂Me CF₃ 2-6 Et H Me OCH₂CH₂OMe SO₂Me 2-7 Et H SO₂Me CO₂Me CN 2-8 Me H Me C(O)SMe SO₂Me 2-9 Me H Me C(O)SEt SO₂Me 2-10 Me H Me 2-(2- SO₂Me oxolanyl)ethoxy 2-11 Me H Me 2-(2-(1,3- SO₂Me dioxolanyl))ethoxy 2-12 Et H Me CH₂OMe SO₂Me 2-13 Et H Me 2-oxolanylmethoxy- SO₂Me methyl 2-14 Me H Cl CO₂Me SO₂Me 2-15 Et H Cl CO₂Me SO₂Et 2-16 Me H Cl C(O)SMe SO₂Me 2-17 Me H Cl C(O)SEt SO₂Me 2-18 Me H Me OMe SO₂Me 2-19 Me H Me OEt SO₂Me 2-20 Me H Me O(i-Pr) SO₂Me 2-21 Me H Me OCHF₂ SO₂Me 2-22 Me H Me (4,5- SO₂Me dihydroisoxazol-3- yl)) 2-23 Me H Me O(n-Pr) SO₂Et 2-24 Me H Cl CH₂OMe SO₂Me 2-25 Me H Me OCO₂Me SO₂Me 2-26 Me H Me OC(O)SMe SO₂Me 2-27 Me H Me OC(O)SEt SO₂Me 2-28 Me H Me OCH₂CH₂OMe SO₂Me 2-29 Et H Me OEt SO₂Me 2-30 Et H Cl CO₂Et SO₂Me 2-31 Et H Cl CO₂(n-Pr) SO₂Me 2-32 Et H Me CO₂Et SO₂Me 2-33 Me H Me CH₂CO₂Me SO₂Me 2-34 Me H Me OCH₂CO₂Et SO₂Me 2-35 Me H Me O(n-Pr) SO₂Me 2-36 Et H SO₂Me H CF₃ 2-37 Me H Me CH₂OCH₂CF₃ SO₂Me 2-38 Me H Cl CH₂OCH₂CF₃ SO₂Me 2-39 Et H Me Cl SO₂Me 2-40 Me H Me CH₂SO₂Me SO₂Me 2-41 Me H Me CH₂OEt SO₂Me 2-42 Me H Cl CH₂OMe SO₂Me 2-43 Me H Me CH₂CH₂OMe SO₂Me 2-44 Me H Me CH₂OCH₂CH₂OMe SO₂Me 2-45 Me H Me OCH₂CH₂OEt SO₂Me 2-46 Me H Me OCH₂CH₂Cl SO₂Me 2-47 Me H Me OCH₂CF₃ SO₂Me 2-48 Me H Me CH₂OCH₂OMe SO₂Me 2-49 Me H Me OCH₂CH₂SMe SO₂Me 2-50 Me H Me CN SO₂Me 2-51 Me H Me CH₂CN SO₂Me 2-52 Me H Br CO₂Me SO₂Me 2-53 Et H Cl CO₂Me SO₂Me 2-54 Me H Br CO₂Me SO₂Me 2-55 Me H Cl OCH₂CH₂OCF₃ SO₂Me 2-56 Et H Cl OCH₂CH₂OCF₃ SO₂Me 2-57 Me H Me OCH₂CH₂OCF₃ SO₂Me 2-58 Et H Me OCH₂CH₂OCF₃ SO₂Me 2-59 Me H CF₃ OCH₂CH₂OCF₃ SO₂Me 2-60 Et H CF₃ OCH₂CH₂OCF₃ SO₂Me 2-61 Me H Br OCH₂CH₂OCF₃ SO₂Me 2-62 Et H Br OCH₂CH₂OCF₃ SO₂Me 2-63 Me H SO₂Me OCH₂CH₂OCF₃ CF₃ 2-64 Et H SO₂Me OCH₂CH₂OCF₃ CF₃ 2-65 Me H Cl OCH₂CH₂OCHClF SO₂Me 2-66 Et H Cl OCH₂CH₂OCHClF SO₂Me 2-67 Me H Me OCH₂CH₂OCHClF SO₂Me 2-68 Et H Me OCH₂CH₂OCHClF SO₂Me 2-69 Me H CF₃ OCH₂CH₂OCHClF SO₂Me 2-70 Et H CF₃ OCH₂CH₂OCHClF SO₂Me 2-71 Me H Br OCH₂CH₂OCHClF SO₂Me 2-72 Et H Br OCH₂CH₂OCHClF SO₂Me 2-73 Me H SO₂Me OCH₂CH₂OCHClF CF₃ 2-74 Et H SO₂Me OCH₂CH₂OCHClF CF₃ 2-75 Me H Cl OCH₂CHFOCF₃ SO₂Me 2-76 Et H Cl OCH₂CHFOCF₃ SO₂Me 2-77 Me H Me OCH₂CHFOCF₃ SO₂Me 2-78 Me H Cl OCH₂CHFOMe SO₂Me 2-79 Et H Cl OCH₂CHFOMe SO₂Me 2-80 Me H Me OCH₂CHFOMe SO₂Me 2-81 Et H Me OCH₂CHFOMe SO₂Me 2-82 Me H CF₃ OCH₂CHFOMe SO₂Me 2-83 Et H CF₃ OCH₂CHFOMe SO₂Me 2-84 Me H Br OCH₂CHFOMe SO₂Me 2-85 Et H Br OCH₂CHFOMe SO₂Me 2-86 Me H SO₂Me OCH₂CHFOMe CF₃ 2-87 Et H SO₂Me OCH₂CHFOMe CF₃ 2-88 Me H Cl OCHFCH₂OCF₃ SO₂Me 2-89 Et H Cl OCHFCH₂OCF₃ SO₂Me 2-90 Me H Cl OCH₂CH₂OCF₂Cl SO₂Me 2-91 Et H Cl OCH₂CH₂OCF₂Cl SO₂Me 2-92 Me H Me OCH₂CH₂OCF₂Cl SO₂Me 2-93 Et H Me OCH₂CH₂OCF₂Cl SO₂Me 2-94 Me H CF₃ OCH₂CH₂OCF₂Cl SO₂Me 2-95 Et H CF₃ OCH₂CH₂OCF₂Cl SO₂Me 2-96 Me H Br OCH₂CH₂OCF₂Cl SO₂Me 2-97 Et H Br OCH₂CH₂OCF₂Cl SO₂Me 2-98 Me H SO₂Me OCH₂CH₂OCF₂Cl CF₃ 2-99 Et H SO₂Me OCH₂CH₂OCF₂Cl CF₃ 2-100 Me H Cl SCH₂CH₂OCH₃ SO₂Me 2-101 Et H Cl SCH₂CH₂OCH₃ SO₂Me 2-102 Me H Me SCH₂CH₂OCH₃ SO₂Me 2-103 Et H Me SCH₂CH₂OCH₃ SO₂Me 2-104 Me H CF₃ SCH₂CH₂OCH₃ SO₂Me 2-105 Et H CF₃ SCH₂CH₂OCH₃ SO₂Me 2-106 Me H Br SCH₂CH₂OCH₃ SO₂Me 2-107 Et H Br SCH₂CH₂OCH₃ SO₂Me 2-108 Me H SO₂Me SCH₂CH₂OCH₃ CF₃ 2-109 Et H SO₂Me SCH₂CH₂OCH₃ CF₃ 2-110 Me H Cl SCH₂CH₂OCF₃ SO₂Me 2-111 Et H Cl SCH₂CH₂OCF₃ SO₂Me 2-112 Me H Me SCH₂CH₂OCF₃ SO₂Me 2-113 Et H Me SCH₂CH₂OCF₃ SO₂Me 2-114 Me H CF₃ SCH₂CH₂OCF₃ SO₂Me 2-115 Et H CF₃ SCH₂CH₂OCF₃ SO₂Me 2-116 Me H Br SCH₂CH₂OCF₃ SO₂Me 2-117 Et H Br SCH₂CH₂OCF₃ SO₂Me 2-118 Me H SO₂Me SCH₂CH₂OCF₃ CF₃ 2-119 Et H SO₂Me SCH₂CH₂OCF₃ CF₃ 2-120 Me H Cl SCH₂CH₂SCH₃ SO₂Me 2-121 Et H Cl SCH₂CH₂SCH₃ SO₂Me 2-122 Me H Me SCH₂CH₂SCH₃ SO₂Me 2-123 Et H Me SCH₂CH₂SCH₃ SO₂Me 2-124 Me H CF₃ SCH₂CH₂SCH₃ SO₂Me 2-125 Et H CF₃ SCH₂CH₂SCH₃ SO₂Me 2-126 Me H Br SCH₂CH₂SCH₃ SO₂Me 2-127 Et H Br SCH₂CH₂SCH₃ SO₂Me 2-128 Me H SO₂Me SCH₂CH₂SCH₃ CF₃ 2-129 Et H SO₂Me SCH₂CH₂SCH₃ CF₃ 2-130 Me H Cl SCH₂CH₂SCF₃ SO₂Me 2-131 Et H Cl SCH₂CH₂SCF₃ SO₂Me 2-132 Me H Me SCH₂CH₂SCF₃ SO₂Me 2-133 Et H Me SCH₂CH₂SCF₃ SO₂Me 2-134 Me H CF₃ SCH₂CH₂SCF₃ SO₂Me 2-135 Et H CF₃ SCH₂CH₂SCF₃ SO₂Me 2-136 Me H Br SCH₂CH₂SCF₃ SO₂Me 2-137 Et H Br SCH₂CH₂SCF₃ SO₂Me 2-138 Me H SO₂Me SCH₂CH₂SCF₃ CF₃ 2-139 Et H SO₂Me SCH₂CH₂SCF₃ CF₃ 2-140 Me H Cl OCH₂CH(CH₃)OCH₃ SO₂Me 2-141 Et H Cl OCH₂CH(CH₃)OCH₃ SO₂Me 2-142 Me H Me OCH₂CH(CH₃)OCH₃ SO₂Me 2-143 Et H Me OCH₂CH(CH₃)OCH₃ SO₂Me 2-144 Me H CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 2-145 Et H CF₃ OCH₂CH(CH₃)OCH₃ SO₂Me 2-146 Me H Br OCH₂CH(CH₃)OCH₃ SO₂Me 2-147 Et H Br OCH₂CH(CH₃)OCH₃ SO₂Me 2-148 Me H SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 2-149 Et H SO₂Me OCH₂CH(CH₃)OCH₃ CF₃ 2-150 Me H Cl OCH₂CF₂OCH₃ SO₂Me 2-151 Et H Cl OCH₂CF₂OCH₃ SO₂Me 2-152 Me H Me OCH₂CF₂OCH₃ SO₂Me 2-153 Et H Me OCH₂CF₂OCH₃ SO₂Me 2-154 Me H CF₃ OCH₂CF₂OCH₃ SO₂Me 2-155 Et H CF₃ OCH₂CF₂OCH₃ SO₂Me 2-156 Me H Br OCH₂CF₂OCH₃ SO₂Me 2-157 Et H Br OCH₂CF₂OCH₃ SO₂Me 2-158 Me H SO₂Me OCH₂CF₂OCH₃ CF₃ 2-159 Et H SO₂Me OCH₂CF₂OCH₃ CF₃ 2-160 Me H Me OCH₂CH₂OCH₃ SO₂Me 2-161 Et H Me OCH₂CH₂OCH₃ SO₂Me 2-162 Me H Me OCH₂CH(OCH₃)₂ SO₂Me 2-163 Me H Me CH₂N(Me)CH₂CN SO₂Me 2-164 Me H Me (tetrahydrofuran-2- SO₂Me yl)methoxy 2-165 Me H Cl SMe SO₂Me 2-166 Me H Cl Cl SO₂Me 2-167 Me H Cl OMe SO₂Me 2-168 Me H Me (tetrahydro-2H- SO₂Me pyran-2-yl)methoxy 2-169 Me H Cl OCH₂CH₂OMe SO₂Me 2-170 Me H Me Tetrahydrofuran-3- SO₂Me yloxy 2-171 Me H Me OCH₂CH₂CH₂OMe SO₂Me 2-172 Me H Me OCH₂CH₂OMe SO₂Me 2-173 Et H Cl (1,3-dioxolan-2-yl) SO₂Me ethoxy 2-174 Me H Me propargyloxy SO₂Me 2-175 Me H Me tetrahydrofuran-3- SO₂Me yloxy)methyl 2-176 Me H Cl SO₂Me SO₂Me 2-177 Me H Me (CH₂)₆Me SO₂Me 2-178 Me H Me CH₂CH₂CH₂OMe SO₂Me 2-179 Et H Cl (1,3-dioxolan-2- SO₂Me yl)methoxy 2-180 Me H Me CH₂N[C(O)SEt]CH₂CN SO₂Me 2-181 Me H Me CHCHCN SO₂Me 2-182 Me H Me CH₂CH₂CN SO₂Me 2-183 Me H Me CH₂SCN SO₂Me 2-184 Me H Me CH₂C(S)NH₂ SO₂Me 2-185 Me H Me OCH₂CH₂OMe SO₂Me 2-186 Et H Me OCH₂CH₂OMe SO₂Me 2-187 Me H Me OCH(CH₃)CH₂OMe SO₂Me 2-188 Me H Me OCH₂CH(Et)OMe SO₂Me 2-189 Me H Me (1,3-dioxolan-2-yl) SO₂Me methyl 2-190 Me H Me CH₂O(i-Pr) SO₂Me

TABLE 4 ¹H-NMR δ ppm (solvent: CDCl₃ unless otherwise specified, measuring instrument: JEOL- GSX (400 MHz) or VARIAN MERCURY plus (300 MHz)/ No. the same applies hereinafter) 2-1 2.32 (s, 3H), 3.13 (s, 3H), 3.61 (s, 3H), 3.93 (s, 3H), 7.28 (s, 1H), 7.56 (d, 1H, J = 7.8 Hz), 7.93 (d, 1H, J = 7.8 Hz), 8.44 (br.s, 1H). 2-2 1.46 (t, 3H), 2.38 (s, 3H), 3.18 (s, 3H), 3.98 (s, 3H), 4.07 (q, 2H), 7.32 (d, 1H, J = 7.8 Hz), 7.61 (s, 1H), 7.98 (d, 1H, J = 7.8 Hz). 2-19 1.48 (t, 3H, J = 7.2 Hz), 2.36 (s, 3H), 3.34 (s, 3H), 3.71 (s, 3H), 4.10 (q, 2H, J = 7.2 Hz), 6.98 (br s, 1H), 7.37 (m, 2H), 7.90 (d, 1H, J = 7.2 Hz). 2-20 1.34 (d, 6H, J = 6.4 Hz), 2.33 (s, 3H), 3.22 (s, 3H), 3.70 (s, 3H), 4.82 (qq, 1H, J = 6.4, 6.4 Hz), 6.90 (br s. 1H), 7.29 (d, 1H, J = 7.6 Hz), 7.33 (s, 1H), 7.94 (d, 1H, J = 7.6 Hz). 2-21 2.43 (s, 3H), 2.23 (s, 3H), 3.71 (s, 3H), 5.30 (br s, 1H), 6.75 (t, 1H, J = 74.8 Hz), 7.33 (s, 1H), 7.50 (d, 1H, J = 8.0 Hz), 8.00 (d, 1H, J = 8.0 Hz). 2-29 1.44 (t, 3H, J = 7.2 Hz), 1.48 (t, 3H, J = 7.2 Hz), 2.36 (s, 3H), 3.27 (s, 3H), 4.06 (q, 2H, J = 7.2 Hz), 4.13 (q, 2H, J = 7.2 Hz), 5.2 (br s, 1H), 7.33 (d, 1H, J = 8.0 Hz), 7.34 (s, 1H), 7.90 (d, 1H, J = 8.0 Hz) 2-30 (Acetone-d₆) 1.30 (br s, 3H), 1.37 (t, 3H, J = 7.0 Hz), 3.25 (s, 3H), 3.95 (br s, 2H), 4.43 (q, 2H, J = 7.0 Hz), 7.27 (br s, 1H), 7.75 (br s, 1H), 8.07 (br s, 1H). 2-31 (Acetone-d₆) 1.18 (t, 3H, J = 7.4 Hz), 1.34 (br s, 3H), 1.80 (m, 2H), 3.25 (s, 3H), 3.98 (br s, 2H), 4.33 (t, 2H, J = 5.6 Hz), 7.32 (br s, 1H), 7.81 (br s, 1H), 8.08 (br s, 1H). 2-33 2.33 (s, 3H), 3.16 (s, 3H), 3.73 (s, 2H), 3.76 (s, 3H), 4.42 (s, 2H), 7.20-7.60 (br s, 1H), 7.34 (s, 1H), 7.52 (d, 1H, J = 8.1 Hz), 8.10 (d, 1H, J = 8.1 Hz). 2-34 1.27 (t, 3H, J = 7.6 Hz), 2.32 (s, 3H), 3.32 (s, 3H), 3.66 (s, 3H), 4.25 (q, 2H, J = 7.6 Hz), 4.61 (s, 2H), 7.30 (s, 1H), 7.35 (d, 1H, J = 8.0 Hz), 7.88 (d, 1H, J = 8.0 Hz). 2-40 (Acetone-d₆) 2.51 (s, 3H), 3.12 (s, 3H), 3.23 (s, 3H), 3.29 (s, 3H), 5.4 (br s, 2H), 6.8 (br s, 1H), 7.42 (d, 1H, J = 8.0 Hz), 8.00 (d, 1H, J = 8.0 Hz). 2-50 2.72 (s, 3H), 3.34 (s, 3H), 3.74 (s, 3H), 5.10-5.60 (br s, 1H), 7.32 (s, 1H), 7.81 (d, 1H, J = 8.1 Hz), 8.16 (d, 1H, J = 8.1 Hz). 2-51 2.53 (s, 3H), 3.24 (s, 3H), 3.74 (s, 3H), 4.47 (s, 2H), 6.70-7.20 (br s, 1H), 7.33 (s, 1H), 7.60 (d, 1H, J = 8.1 Hz), 8.14 (d, 1H, J = 8.1 Hz). 2-53 1.42 (t, 3H, J = 7.3 Hz), 3.20 (s, 3H), 4.04 (s, 3H), 4.09 (q, 2H, J = 7.3 Hz), 7.34 (s, 1H), 7.64 (d, 1H, J = 7.8 Hz), 8.07 (d, 1H, J = 7.8 Hz). 2-142 1.23 (d, 3H, J = 6.4 Hz), 2.34 (s, 3H), 3.24 (s, 3H), 3.41 (s, 3H), 3.65 (s, 3H), 3.77 (m, 2H), 3.99 (dd, 1H, J = 9.2, 4.0 Hz), 4.05 (dd, 1H, J = 9.2, 6.4 Hz), 7.28 (s, 1H), 7.29 (d, 1H, J = 8.4 Hz), 7.86 (d, 1H, J = 8.4 Hz). 2-161 1.40 (t, 3H, J = 7.0 Hz), 2.39 (s, 3H), 3.23 (s, 3H), 3.43 (s, 3H), 3.76 (m, 2H), 4.21 (q, 1H, J = 7.0 Hz), 4.19 (m, 2H), 7.29 (s, 1H), 7.31 (d, 1H, J = 8.0 Hz), 7.83 (d, 1H, J = 8.0 Hz). 2-163 2.41 (s, 3H), 2.48 (s, 3H), 3.27 (s, 3H), 3.63 (s, 2H), 3.72 (s, 3H), 4.23 (s, 2H), 7.29 (s, 1H), 7.51 (d, 1H, J = 8.1 Hz), 8.12 (d, 1H, J = 8.1 Hz). 2-166 2.55 (s, 3H), 3.45 (s, 3H), 7.29-7.33 (m, 2H), 7.35 (d, 1H, J = 8.4 Hz). 2-173 1.43 (t, 3H, J = 7.3 Hz), 2.28 (m, 2H), 3.29 (s, 3H), 3.86 (m, 2H), 3.96 (m, 2H), 4.08 (m, 2H), 4.39 (m, 2H), 5.13 (t, 1H, J = 5.5 Hz), 7.32 (s, 1H), 7.33 (d, 1H, J = 7.8 Hz), 7.96 (d, 1H, J = 7.8 Hz). 2-176 2.49 (s, 3H), 3.54 (s, 3H), 3.57 (s, 3H), 7.40 (s, 1H), 7.63 (d, 1H, J = 7.6 Hz), 8.06 (d, 1H, J = 7.6 Hz). 2-179 1.42 (t, 3H, J = 7.3 Hz), 3.35 (s, 3H), 3.95 (m, 2H), 4.04-4.12 (m, 4H), 4.29 (m, 2H), 5.46 (t, 1H, J = 5.5 Hz), 7.32 (s, 1H), 7.36 (d, 1H, J = 7.8 Hz), 7.98 (d, 1H, J = 7.8 Hz). 2-183 2.58 (s, 3H), 2.80-3.20 (br s, 1H), 3.25 (s, 3H), 3.73 (s, 3H), 4.89 (s, 2H), 7.33 (s, 1H), 7.58 (d, 1H, J = 8.1 Hz), 8.07 (d, 1H, J = 8.1 Hz). 2-184 2.50 (s, 3H), 3.20 (s, 3H), 3.72 (s, 3H), 4.66 (s, 2H), 7.32 (s, 1H), 7.40-7.50 (br s, 1H), 7.52 (d, 1H, J = 8.1 Hz), 8.11 (d, 1H, J = 8.1 Hz). 2-187 1.25 (t, 3H, J = 7.3 Hz), 2.35 (s, 3H), 3.25 (s, 3H), 3.34 (s, 3H), 3.53 (m, 1H), 3.70 (s, 3H), 3.74 (m, 1H), 4.88 (m, 1H), 7.24 (s, 1H), 7.31 (d, 1H, J = 7.8 Hz), 7.85 (d, 1H, J = 7.8 Hz). 2-189 2.41 (s, 3H), 3.14 (s, 3H), 3.61 (d, 2H, J = 5.2 Hz), 3.65 (s, 3H), 3.77-3.82 (m, 2H), 3.88-3.96 (m, 2H), 5.12 (t, 1H, J = 4.8 Hz), 5.45 (br s, 1H), 7.24 (s, 1H), 7.37 (d, 1H, J = 8.0 Hz), 8.01 (d, 1H, J = 8.0 Hz). 2-190 1.25 (d, 6H, J = 6.4 Hz), 1.44 (t, 3H, J = 7.4 Hz), 2.47 (s, 3H), 3.25 (s, 3H), 3.83 (m, 1H), 4.06 (q, 2H, J = 7.4 Hz), 4.7 (br s, 1H), 5.00 (s, 2H), 7.31 (s, 1H), 7.50 (d, 1H, J = 8.4 Hz), 8.07 (d, 1H, J = 8.4 Hz).

Now, Test Examples will be described.

Test Example 1

Upland field soil was put into a 1/170,000 hectare pot, and seeds of various plants were sown. When the respective plants reached predetermined leaf stage ((1) barnyardgrass (Echinochloa crus-galli L.); 0.8 to 2.5 leaf stage, (2) crabgrass (Digitaria sanguinalis L.): 0.5 to 3.0 leaf stage, (3) greenfoxtail (Setaria viridis L.): 1.0 to 3.0 leaf stage, (4) redroot pigweed (Amaranthus retroflexus L.): cotyledon stage to 2.0 leaf stage, (5) prickly sida (Sida spinosa L.): cotyledon stage to 1.1 leaf stage, (6) velvetleaf (Abutilon theophrasti MEDIC.): cotyledon stage to 1.5 leaf stage, (7) rice (Oryza sativa L.): 1.0 to 2.5 leaf stage, (8) wheat (Triticum spp.): 1.7 to 3.4 leaf stage, (9) corn (Zea mays L.): 2.0 to 3.5 leaf stage, and (10) soybean (Glycine max Merr.): primary leaf stage to 0.3 leaf stage), wettable powders or emulsifiable concentrates of the compounds of the present invention prepared in accordance with a conventional preparation method, were weighed so that the active ingredients became the prescribed amounts, and diluted with water in an amount corresponding to 500 liter per 1 hectare. 0.1 vol % of an agricultural spreader was further added to the respective diluted liquids, followed by foliar treatment with a small sprayer.

On the 17th to 23rd day after application, the state of growth of the respective plants was visually observed, and the herbicidal effect was evaluated in accordance with a growth inhibition rate (%) of 0 (equivalent to the non-treated area) to 100% (complete kill). The results are shown in Table 5.

TABLE 5 Growth inhibition rate (%) Amount of active ingredient redroot Date No. (g/ha) Barnyardgrass Crabgrass Greenfoxtail pigweed Prickly sida Velvetleaf Rice Wheat Corn Soybean of observation 1 31 90 80 100 100 70 100 80 0 10 — 20 2 31 95 90 100 95 95 95 95 30 10 — 20 3 31 95 95 100 90 90 95 100 50 60 95 22 4 31 95 95 100 — 80 95 100 50 5 95 23 16 31 100 100 100 — 40 100 90 0 0 95 21 27 31 100 80 100 95 70 80 80 10 40 90 22 29 31 80 50 50 70 60 65 40 0 10 60 20 31 31 100 30 80 70 70 60 60 0 60 50 22 35 31 90 80 100 90 40 80 80 0 0 90 21 36 31 100 98 100 100 100 100 70 50 10 — 21 37 31 95 80 100 100 — 95 70 0 0 70 21 38 31 80 0 30 20 40 60 40 0 0 70 21 39 31 95 90 95 80 — 90 95 40 0 95 21 40 31 95 80 95 90 70 90 70 0 10 90 23 42 31 100 98 95 100 90 95 90 0 0 95 22 55 31 100 100 100 95 — 100 60 10 40 95 20 58 31 95 98 100 90 70 100 80 40 0 98 20 59 31 90 80 70 80 80 75 50 10 0 70 21 60 31 95 90 60 80 70 70 70 0 0 50 21 61 31 98 98 100 100 95 95 90 60 50 80 21 62 31 100 100 100 100 — 95 80 50 10 90 20 63 31 95 98 100 95 — 95 90 10 0 95 20 64 31 100 — 65 80 60 85 70 0 0 — 20 65 31 20 10 10 30 30 50 0 0 0 10 20 66 31 95 98 100 95 75 95 60 10 0 98 21 67 31 95 98 100 95 60 90 60 10 10 90 21 68 31 95 40 60 75 70 80 60 0 10 70 21 69 31 95 98 95 85 70 95 80 0 50 98 21 70 31 100 100 100 100 70 80 70 0 30 80 22 71 31 70 40 60 70 60 60 60 10 0 60 22 72 31 80 50 70 60 60 60 50 0 10 70 22 73 31 100 100 100 100 70 98 95 0 30 98 22 74 31 100 98 80 100 70 100 95 20 40 98 21 75 31 98 100 100 100 100 100 98 0 40 98 21 76 31 98 98 80 90 65 75 60 0 30 95 21 77 31 98 98 98 95 70 80 70 0 10 95 21 78 31 60 70 60 60 60 65 10 0 0 70 21 79 31 100 100 98 100 75 98 60 0 50 100 21 82 31 70 40 60 60 50 70 40 0 0 70 22 81 31 30 0 0 10 0 0 10 0 10 50 20 83 31 100 100 100 80 70 95 80 0 0 95 22 84 31 98 98 100 100 100 95 95 50 10 95 21 85 31 98 98 100 95 98 98 95 60 10 98 21 86 31 95 90 95 95 80 95 95 20 30 85 20 87 31 95 100 100 100 75 95 90 10 10 95 20 88 31 98 95 100 95 90 95 95 10 20 95 21 89 31 100 100 100 90 60 100 100 20 20 95 20 90 31 80 60 95 80 75 95 40 0 0 80 21 91 31 95 98 98 98 75 95 90 0 20 98 21 92 31 0 0 60 10 10 70 0 0 0 10 22 93 31 95 80 95 98 70 80 70 0 30 80 22 95 31 100 90 100 100 80 90 90 20 10 95 22 97 31 100 70 100 100 50 80 60 10 0 80 22 99 31 98 100 100 98 100 98 95 60 50 98 21 101 31 100 100 100 100 70 98 98 10 30 90 22 189 31 95 95 98 — 70 100 90 — 0 98 21 207 31 95 95 100 100 60 100 70 0 0 100 21 208 31 95 100 100 100 40 95 80 0 0 100 21 209 31 100 95 98 98 90 100 95 0 0 100 17 210 31 80 30 50 10 70 60 50 0 0 50 22 211 31 70 70 70 90 20 90 50 0 20 98 20 212 63 100 50 60 100 40 60 30 0 0 90 20 213 125 98 70 50 80 60 70 60 30 0 95 20 214 63 98 95 90 100 70 80 90 0 0 100 20 215 31 100 60 70 95 50 50 70 0 30 95 20 216 31 100 100 98 100 50 98 70 0 10 95 20 217 31 100 100 98 100 70 80 90 40 0 98 21 218 31 100 100 95 100 70 90 98 10 0 95 21 219 31 100 100 100 100 70 100 80 0 0 100 21 220 63 100 60 70 100 90 90 80 0 0 100 21 221 63 100 50 50 80 40 60 20 0 0 100 21 222 31 90 70 80 100 30 60 70 0 0 100 21 223 31 100 100 90 90 70 95 70 0 0 100 21 224 63 95 60 70 95 70 60 20 0 0 100 21 225 31 30 0 20 0 0 0 0 0 0 50 21 226 31 100 95 95 95 70 80 100 0 0 100 21 227 63 100 100 100 100 60 100 30 0 0 95 21 228 63 98 60 40 40 40 70 0 0 0 80 21 229 63 100 100 100 100 98 100 95 50 60 98 21 230 63 100 100 100 100 80 95 95 40 0 100 22 231 63 100 70 40 80 40 80 50 0 0 100 22 232 63 90 95 95 — 70 90 95 0 0 90 21 233 31 100 100 100 — 60 100 80 0 0 100 21 234 31 100 100 100 100 50 100 90 0 0 100 21 235 31 100 100 100 100 50 100 90 40 30 100 21 236 31 60 50 40 90 40 70 80 0 0 95 21 238 63 100 98 98 100 98 100 90 10 0 98 17 239 31 98 100 100 — 80 100 85 — 0 100 21 241 31 100 98 100 100 90 100 90 — 0 100 21

Test Example 2

Upland field soil was put into a 1/170,000 hectare pot, and seeds of various plants (barnyardgrass, crabgrass, greenfoxtail, redroot pigweed, prickly sida, velvetleaf, rice, wheat, corn and soybean) were sown. On the day after sowing, wettable powders or emulsifiable concentrates of the compounds of the present invention prepared in accordance with a conventional preparation method, were weighed so that the active ingredients became the prescribed amounts, and diluted with water in an amount corresponding to 500 liter per 1 hectare, followed by soil application with a small sprayer.

On the 19th to 24th day after the application, the state of growth of the respective plants was visually observed, and the herbicidal effect was evaluated in accordance with a growth inhibition rate (%) of from 0 (equivalent to the non-treated area) to 100% (complete kill). The results are shown in Table 6.

TABLE 6 Growth inhibition rate (%) Amount of active ingredient redroot Date No. (g/ha) Barnyardgrass Crabgrass Greenfoxtail pigweed Prickly sida Velvetleaf Rice Wheat Corn Soybean of observation 1 250 100 100 100 100 60 60 95 10 0 75 21 2 250 100 100 98 100 95 60 100 40 0 — 21 3 250 60 100 60 100 95 70 95 0 0 40 21 4 250 80 100 70 100 70 60 70 0 0 50 24 16 250 100 100 98 100 10 0 98 0 0 — 20 27 250 100 95 98 100 100 95 90 10 0 0 20 29 250 50 10 40 — 60 50 10 0 0 40 21 31 250 60 65 70 60 70 60 60 0 0 — 20 35 250 90 100 70 95 90 20 90 0 0 0 22 36 250 100 100 100 100 60 50 80 0 0 30 20 37 250 60 80 60 50 10 30 10 0 0 0 21 38 250 90 95 70 90 70 20 60 0 0 0 22 39 250 70 100 80 100 70 60 80 0 10 0 21 40 250 100 100 100 100 85 90 90 10 0 60 24 42 250 — 100 — 100 — 70 — — 0 — 21 55 250 100 100 100 100 70 95 70 0 0 0 19 58 250 60 100 70 90 70 10 70 0 0 0 21 59 250 100 100 100 100 98 100 80 10 0 10 19 60 250 100 100 60 95 70 60 40 0 0 20 19 61 250 100 100 100 100 80 90 85 30 0 20 19 62 250 80 95 95 100 90 90 70 30 0 0 19 63 250 95 95 90 90 80 70 80 0 0 0 19 64 250 90 95 50 80 60 30 70 0 0 0 19 65 250 0 10 10 20 0 0 0 0 0 0 21 66 250 80 90 40 95 90 40 90 0 0 0 21 67 250 60 70 40 50 70 60 60 0 0 20 20 68 250 100 60 30 98 95 100 100 0 0 40 21 69 250 70 95 50 100 70 70 70 0 0 — 20 70 250 70 80 50 100 65 70 40 0 0 0 20 72 250 — 0 — 50 — 30 — — 0 — 21 73 250 — 100 — 100 — 100 — — 0 — 21 74 250 — 90 — 95 — 70 — — 0 — 21 75 250 — 100 — 100 — 80 — — 10 — 21 76 250 — 100 — 90 — 30 — — 0 — 21 77 250 — 95 — 90 — 40 — — 0 — 21 78 250 — 95 — 80 — 50 — — 0 — 21 79 250 — 90 — 90 — 50 — — 0 — 21 81 250 0 0 10 0 0 0 0 0 0 0 20 82 250 30 70 20 50 80 20 10 0 0 0 21 83 250 80 95 40 90 70 40 50 0 0 0 21 84 250 98 100 100 100 98 98 98 0 30 50 21 85 250 100 100 100 98 100 100 100 0 10 50 21 86 250 95 100 95 100 90 95 90 0 0 0 19 87 250 80 90 70 95 70 50 80 0 0 0 19 88 250 100 100 98 100 95 100 95 0 0 0 20 89 250 70 95 80 90 50 70 80 0 0 0 19 90 250 100 100 100 100 98 100 100 0 10 30 21 91 250 90 95 60 100 95 70 80 0 0 30 20 92 250 80 95 70 70 60 50 80 0 0 0 20 93 250 95 90 100 100 75 65 90 0 0 0 20 95 250 100 95 100 100 95 80 98 0 0 0 20 97 250 100 100 100 100 100 100 70 0 0 10 20 99 250 100 100 100 95 100 100 100 0 0 40 20 189 250 100 100 100 100 100 100 100 — 0 10 20 207 250 100 100 100 100 60 100 98 0 0 20 20 208 250 100 100 100 100 30 50 98 0 0 0 20 209 250 95 95 100 95 30 50 90 20 0 — 20 210 250 0 10 0 20 40 0 0 0 0 0 20 211 250 60 98 60 100 70 40 50 0 0 0 20 212 250 50 40 0 80 50 0 0 0 0 0 21 213 250 50 40 20 30 0 0 0 0 0 0 21 214 250 100 100 100 90 90 90 100 0 0 20 21 215 250 90 95 70 60 40 0 90 0 0 — 21 216 250 95 100 100 100 80 90 80 0 0 0 21 217 250 80 95 60 95 60 20 80 0 0 0 19 218 250 90 80 90 100 50 30 80 0 0 0 19 219 250 100 100 100 100 80 100 95 0 0 0 19 220 250 95 95 100 100 95 95 100 0 0 0 19 221 250 80 100 70 100 60 60 80 0 0 0 19 222 250 95 100 80 100 50 80 90 0 0 0 19 223 250 70 100 70 90 60 80 40 0 0 0 19 224 250 100 100 98 100 75 70 98 — 10 50 20 225 250 0 0 0 30 0 0 0 0 0 0 19 231 250 70 60 0 50 0 0 0 — 0 0 20 233 250 100 100 100 100 40 100 100 — 0 50 20 234 250 100 100 100 100 20 70 100 — 0 0 20 235 250 100 100 100 100 98 20 100 — 0 0 20 236 250 98 95 10 100 30 0 70 — 0 0 20

Now, Formulation Examples of the present invention will be described.

Formulation Example 1

(1) The compound of the present invention 75 parts by weight (2) Geropon T-77 (tradename, manufactured by 14.5 parts by weight Rhone-Poulenc) 3) NaCl 10 parts by weight 4) Dextrin 0.5 part by weight

The above components are placed in a high-speed mixing granulator, admixed with 20 wt % of water, granulated, and dried to obtain water-dispersible granules.

Formulation Example 2

(1) Kaolin 78 parts by weight (2) Laveline FAN (tradename, manufactured by 2 parts by weight DAI-ICHI KOGYO SEIYAKU CO., LTD.) (3) Sorpol 5039 (tradename, manufactured by 5 parts by weight TOHO Chemical Industry Co., Ltd.) (4) Carplex (tradename, manufactured by 15 parts by weight DSL. Japan Co., Ltd.)

The mixture of the above components (1) to (4) and the compound of the present invention are mixed in a weight ratio of 9:1 to obtain a wettable powder.

Formulation Example 3

(1) Hi-Filler No. 10 (tradename, manufactured by 33 parts by weight Matsumura Sangyo Co., Ltd.) (2) Sorpol 5050 (tradename, manufactured by 3 parts by weight TOHO Chemical Industry Co., Ltd.) (3) Sorpol 5073 (tradename, manufactured by 4 parts by weight TOHO Chemical Industry Co., Ltd.) (4) The compound of the present invention 60 parts by weight

The above compounds (1) to (4) are mixed to obtain a wettable powder.

Formulation Example 4

(1) The compound of the present invention 4 parts by weight (2) Bentonite 30 parts by weight (3) Calcium carbonate 61.5 parts by weight (4) Toxanon GR-31A (tradename, manufactured 3 parts by weight by Sanyo Chemical Industries Co., Ltd.) (5) Calcium lignin sulfonate 1.5 parts by weight

Pulverized component (1) and components (2) and (3) are preliminarily mixed, and then components (4) and (5) and water are mixed thereto. The mixture is extruded and granulated, followed by drying and sieving to obtain granules.

Formulation Example 5

(1) The compound of the present invention 30 parts by weight (2) Zieclite (tradename, manufactured by 60 parts by weight Zieclite Co., Ltd.) (3) New Kalgen WG-1 (tradename, manufactured by 5 parts by weight TAKEMOTO OIL & FAT CO., LTD.) (4) New Kalgen FS-7 (tradename, manufactured by 5 parts by weight TAKEMOTO OIL & FAT CO., LTD.)

Components (1), (2) and (3) are mixed and passed through a pulverizer, and then component (4) is added thereto. The mixture is kneaded and then extruded and granulated, followed by drying and sieving to obtain water dispersible granules.

Formulation Example 6

(1) The compound of the present invention 28 parts by weight (2) Soprophor FL (tradename, manufactured by 2 parts by weight Rhone-Poulenc) (3) Sorpol 335 (tradename, manufactured by 1 part by weight TOHO Chemical Industry Co., Ltd.) (4) IP solvent 1620 (tradename, manufactured by 32 parts by weight Idemitsu Petrochemical Co., Ltd.) (5) Ethylene glycol 6 parts by weight (6) Water 31 parts by weight

The above components (1) to (6) are mixed and pulverized by a wet-grinding machine (Dyno-mill) to obtain a water-based suspension concentrate. 

1. A benzoylpyrazole compound represented by the formula (I) or its salt:

wherein R¹ is alkyl or cycloalkyl; R² is a hydrogen atom or alkyl; R³ is alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkenyl, or arylalkyl which may be substituted by R⁸; R⁴ is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R⁵ is a hydrogen atom, alkyl, alkenyl, alkynyl, halogen, cyano, cyanoalkyl, cyanoalkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷, thiocyanatoalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkoxyhaloalkylthio, haloalkoxyhaloalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthiohaloalkylthio, haloalkylthiohaloalkylthio, alkylthioalkoxy, alkylsulfonyl, alkylsulfonylalkyl, alkoxycarbonylalkyl alkoxycarbonylalkoxy, heterocyclylalkyl, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, heterocyclyloxyalkyl, cycloalkyloxy, —OC(O)SR⁷, —OC(O)OR⁷, —C(O)OR⁷, —C(O)SR⁷, —C(S)OR⁷, —C(S)SR⁷, or aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷; R⁶ is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R⁷ is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R¹⁰; and each of R⁸, R⁹ and R¹⁰ which are independent of one another, is halogen, alkyl, or alkoxy.
 2. The benzoylpyrazole compound or its salt according to claim 1, wherein R¹ is alkyl or cycloalkyl; R² is a hydrogen atom or alkyl; R³ is alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkenyl, or arylalkyl which may be substituted by R⁸; R⁴ is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R⁵ is a hydrogen atom, alkyl, halogen, cyano, cyanoalkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthioalkoxy, alkylsulfonyl, alkylsulfonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, —OC(O)SR⁷, —OC(O)OR⁷, —C(O)OR⁷, or —C(O)SR⁷; R⁶ is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R⁷ is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R¹⁰; and each of R⁸, R⁹ and R¹⁰ which are independent of one another, is halogen; alkyl; or alkoxy.
 3. The benzoylpyrazole compound or its salt according to claim 2, wherein R¹ is alkyl or cycloalkyl; R² is a hydrogen atom or alkyl; R³ is alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, or arylalkyl which may be substituted by R⁸; R⁴ is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio alkylsulfinyl, or alkylsulfonyl; R⁵ is alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, —OC(O)SR⁷, —OC(O)OR⁷, —C(O)OR⁷, or —C(O)SR⁷; R⁶ is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R⁷ is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R¹⁰; and each of R⁸, R⁹ and R¹⁰ which are independent of one another, is halogen; alkyl; or alkoxy.
 4. The benzoylpyrazole compound or its salt according to claim 3, wherein R¹ is alkyl; R² is a hydrogen atom; R³ is alkyl; R⁴ is alkyl; R⁵ is alkoxy, haloalkoxy, or —C(O)OR⁷; and R⁶ is alkylsulfonyl.
 5. A process for producing a benzoylpyrazole compound represented by the formula (I) or its salt:

wherein R¹ is alkyl or cycloalkyl; R² is a hydrogen atom or alkyl; R³ is alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkenyl, or arylalkyl which may be substituted by R⁸; R⁴ is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R⁵ is a hydrogen atom, alkyl, alkenyl, alkynyl, halogen, cyano, cyanoalkyl, cyanoalkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷, thiocyanatoalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkoxyhaloalkylthio, haloalkoxyhaloalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthiohaloalkylthio, haloalkylthiohaloalkylthio, alkylthioalkoxy, alkylsulfonyl, alkylsulfonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, heterocyclylalkyl, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, heterocyclyloxyalkyl, cycloalkyloxy, OC(O)SR⁷, —OC(O)OR⁷, —C(O)OR⁷, —C(O)SR⁷, —C(S)OR⁷, —C(S)SR⁷, or aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷; R⁶ is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl, R⁷ is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R¹⁰; and each of R⁸, R⁹ and R¹⁰ which are independent of one another, is halogen, alkyl, or alkoxy, which comprises (1) reacting a compound represented by the formula (II):

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above, with a compound represented by the formula (III):

wherein R³ is as defined above, and Z is a leaving group, (2) reacting a compound represented by the formula (IV-a) and/or the formula (V-a):

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above, with a compound represented by the formula (VI-a): HS—R^(3-a)  (VI-a) wherein R^(3-a) is alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkenyl, or arylalkyl which may be substituted by R⁸, or (3) reacting a compound represented by the formula (IV-b) and/or the formula (V-b):

wherein R¹, R², R⁴, R⁵ and R⁶ are as defined above, with a compound represented by the formula (VI-b): HO—R^(3-b)  (VI-b) wherein R^(3-b) is alkenyl.
 6. A herbicide comprising the benzoylpyrazole compound or its salt as defined in claim 1 as an active ingredient.
 7. A method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the benzoylpyrazole compound or its salt as defined in claim 1 to the undesired plants or to a place where they grow. 